MX2007000428A - Tetrahidroisoquinolinas sustituidas con arilo y heteroarilo y uso de las mismas para bloquear la captacion de norepinefrina, dopamina y serotonina. - Google Patents
Tetrahidroisoquinolinas sustituidas con arilo y heteroarilo y uso de las mismas para bloquear la captacion de norepinefrina, dopamina y serotonina.Info
- Publication number
- MX2007000428A MX2007000428A MX2007000428A MX2007000428A MX2007000428A MX 2007000428 A MX2007000428 A MX 2007000428A MX 2007000428 A MX2007000428 A MX 2007000428A MX 2007000428 A MX2007000428 A MX 2007000428A MX 2007000428 A MX2007000428 A MX 2007000428A
- Authority
- MX
- Mexico
- Prior art keywords
- methyl
- tetrahydroisoquinoline
- carbon atoms
- thiophen
- benzo
- Prior art date
Links
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 title claims description 38
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 title claims description 32
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 title claims description 21
- 229960002748 norepinephrine Drugs 0.000 title claims description 21
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 title claims description 21
- 229960003638 dopamine Drugs 0.000 title claims description 16
- 229940076279 serotonin Drugs 0.000 title claims description 10
- 150000003526 tetrahydroisoquinolines Chemical class 0.000 title 1
- -1 benzoisothiazolyl Chemical group 0.000 claims abstract description 1668
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 1141
- 125000001424 substituent group Chemical group 0.000 claims abstract description 171
- 150000001875 compounds Chemical class 0.000 claims abstract description 149
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 63
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims abstract description 42
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 38
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 32
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims abstract description 32
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 32
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 29
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims abstract description 28
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 28
- 125000001041 indolyl group Chemical group 0.000 claims abstract description 28
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims abstract description 28
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims abstract description 28
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 27
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims abstract description 27
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims abstract description 25
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract description 25
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims abstract description 18
- 125000005872 benzooxazolyl group Chemical group 0.000 claims abstract description 14
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims abstract description 14
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims abstract description 14
- 125000005436 dihydrobenzothiophenyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims abstract description 14
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 14
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims abstract description 14
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims abstract description 14
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims abstract description 14
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims abstract description 13
- 125000005605 benzo group Chemical group 0.000 claims abstract description 11
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims abstract description 11
- 239000000126 substance Substances 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 346
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 242
- 229910052736 halogen Inorganic materials 0.000 claims description 210
- 150000002367 halogens Chemical class 0.000 claims description 210
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 151
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 150
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 137
- 125000001188 haloalkyl group Chemical group 0.000 claims description 131
- 229910052739 hydrogen Inorganic materials 0.000 claims description 130
- 125000003342 alkenyl group Chemical group 0.000 claims description 126
- 125000000304 alkynyl group Chemical group 0.000 claims description 126
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 123
- 239000001257 hydrogen Substances 0.000 claims description 122
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 90
- 125000003545 alkoxy group Chemical group 0.000 claims description 85
- 125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 claims description 72
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 62
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 60
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 60
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 60
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 59
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 44
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 208000035475 disorder Diseases 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 31
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 30
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 30
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 27
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 23
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 19
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 18
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 17
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 15
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 14
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 14
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 14
- 150000001721 carbon Chemical group 0.000 claims description 14
- 125000002541 furyl group Chemical group 0.000 claims description 14
- 125000002883 imidazolyl group Chemical group 0.000 claims description 14
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 14
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 14
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 14
- 125000002971 oxazolyl group Chemical group 0.000 claims description 14
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 14
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 14
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 14
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 14
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 14
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 14
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 14
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 14
- 125000000335 thiazolyl group Chemical group 0.000 claims description 14
- 125000001425 triazolyl group Chemical group 0.000 claims description 14
- 125000002471 4H-quinolizinyl group Chemical group C=1(C=CCN2C=CC=CC12)* 0.000 claims description 13
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 13
- 125000001819 4H-chromenyl group Chemical group O1C(=CCC2=CC=CC=C12)* 0.000 claims description 12
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 125000000850 2H-chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 10
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 10
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 10
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 8
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
- GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 claims description 6
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004532 benzofuran-3-yl group Chemical group O1C=C(C2=C1C=CC=C2)* 0.000 claims description 6
- 125000004540 benzothiazol-5-yl group Chemical group S1C=NC2=C1C=CC(=C2)* 0.000 claims description 6
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
- 125000004247 indolizin-1-yl group Chemical group [H]C1=C([H])C(*)=C2C([H])=C([H])C([H])=C([H])N12 0.000 claims description 5
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 4
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 4
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000004538 indolizin-3-yl group Chemical group C=1C=C(N2C=CC=CC12)* 0.000 claims description 4
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000004260 quinazolin-2-yl group Chemical group [H]C1=NC(*)=NC2=C1C([H])=C([H])C([H])=C2[H] 0.000 claims description 4
- 125000004546 quinazolin-4-yl group Chemical group N1=CN=C(C2=CC=CC=C12)* 0.000 claims description 4
- 125000004547 quinazolin-6-yl group Chemical group N1=CN=CC2=CC(=CC=C12)* 0.000 claims description 4
- 201000009032 substance abuse Diseases 0.000 claims description 4
- 208000011117 substance-related disease Diseases 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 3
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 3
- 230000003247 decreasing effect Effects 0.000 claims description 3
- 230000006735 deficit Effects 0.000 claims description 3
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 claims description 3
- 231100000736 substance abuse Toxicity 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- ZQTSWBZQPURWCA-UHFFFAOYSA-N 1-[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]pyridin-2-one Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1N1C=CC=CC1=O ZQTSWBZQPURWCA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- KEIXRHLMPMEEQH-UHFFFAOYSA-N 2-[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-1,3-thiazole Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1C1=NC=CS1 KEIXRHLMPMEEQH-UHFFFAOYSA-N 0.000 claims description 2
- DRWBXGJOUMYWQP-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-1-methyl-1,2,3,4-tetrahydroisoquinoline Chemical compound C12=CC=CC=C2C(C)NCC1C1=CC2=CC=CC=C2S1 DRWBXGJOUMYWQP-UHFFFAOYSA-N 0.000 claims description 2
- QWQHWOULDSABHO-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-2-methyl-1,3-dihydroisoquinolin-4-ol Chemical compound C1=CC=C2SC(C3(O)C4=CC=CC=C4CN(C3)C)=CC2=C1 QWQHWOULDSABHO-UHFFFAOYSA-N 0.000 claims description 2
- JPZRMBVYXPVWTO-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-ol Chemical compound C12=CC=C(O)C=C2CN(C)CC1C1=CC2=CC=CC=C2S1 JPZRMBVYXPVWTO-UHFFFAOYSA-N 0.000 claims description 2
- FTGCXJUERZVKRX-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-2-methyl-7-(6-methylpyrazin-2-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1C1=CN=CC(C)=N1 FTGCXJUERZVKRX-UHFFFAOYSA-N 0.000 claims description 2
- SHZIVSOSKOIXMU-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-2-methyl-7-pyrazin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1C1=CN=CC=N1 SHZIVSOSKOIXMU-UHFFFAOYSA-N 0.000 claims description 2
- LXGKFXLBRARNJV-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-7-(3-methoxypyrazin-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=NC=CN=C1C1=CC=C(C(CN(C)C2)C=3SC4=CC=CC=C4C=3)C2=C1 LXGKFXLBRARNJV-UHFFFAOYSA-N 0.000 claims description 2
- VOYRKEITBFDOOG-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-7-(6-methoxypyrazin-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=CN=CC(C=2C=C3CN(C)CC(C3=CC=2)C=2SC3=CC=CC=C3C=2)=N1 VOYRKEITBFDOOG-UHFFFAOYSA-N 0.000 claims description 2
- JTHIDGXKIIJPMD-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2-methyl-7-(3-methylpyrazin-2-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=NC=CN=C1C JTHIDGXKIIJPMD-UHFFFAOYSA-N 0.000 claims description 2
- VZRYQPFTDLHBPC-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2-methyl-7-pyrazin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=CN=CC=N1 VZRYQPFTDLHBPC-UHFFFAOYSA-N 0.000 claims description 2
- NRDMFZVUBYELSH-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2-methyl-7-pyrimidin-4-yl-3,4-dihydro-1H-isoquinolin-8-ol Chemical compound OC1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=CC=NC=N1 NRDMFZVUBYELSH-UHFFFAOYSA-N 0.000 claims description 2
- DELHGKQNJWIBFE-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-7-methoxy-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2SC=CC2=CC(C2C3=CC=C(C=C3CN(C)C2)OC)=C1 DELHGKQNJWIBFE-UHFFFAOYSA-N 0.000 claims description 2
- ZVVLDVHEXXOHIP-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-8-methoxy-2-methyl-7-pyrimidin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=NC=CC=N1 ZVVLDVHEXXOHIP-UHFFFAOYSA-N 0.000 claims description 2
- SFGBUAZWRDEXOF-UHFFFAOYSA-N 4-(4-chloro-1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC2=C(Cl)C=CC=C2S1 SFGBUAZWRDEXOF-UHFFFAOYSA-N 0.000 claims description 2
- XJESWCUEYBDVIF-UHFFFAOYSA-N 4-(4-fluoro-1-benzothiophen-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC(F)=C4C=3)C2=CC=C1C1=CC=CN=N1 XJESWCUEYBDVIF-UHFFFAOYSA-N 0.000 claims description 2
- XMPBEPHPYKAAHW-UHFFFAOYSA-N 4-(5-methoxy-1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C1N(C)CC2=CC=CC=C2C1C1=CC2=CC(OC)=CC=C2S1 XMPBEPHPYKAAHW-UHFFFAOYSA-N 0.000 claims description 2
- MVUZWCXBSYGQNK-UHFFFAOYSA-N 4-(6-methoxy-1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C1N(C)CC2=CC=CC=C2C1C1=CC2=CC=C(OC)C=C2S1 MVUZWCXBSYGQNK-UHFFFAOYSA-N 0.000 claims description 2
- KTNYYVXPLRKWRF-UHFFFAOYSA-N 4-(7-fluoro-1-benzothiophen-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3SC4=C(F)C=CC=C4C=3)C2=CC=C1C1=CC=CN=N1 KTNYYVXPLRKWRF-UHFFFAOYSA-N 0.000 claims description 2
- QMEVHQYFJCWPEI-UHFFFAOYSA-N 4-(7-methoxy-1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C1N(C)CC2=CC=CC=C2C1C1=CC(C=CC=C2OC)=C2S1 QMEVHQYFJCWPEI-UHFFFAOYSA-N 0.000 claims description 2
- HHHHRYUBBZKZLS-UHFFFAOYSA-N 4-[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-2,6-dimethylmorpholine Chemical compound C1C(C)OC(C)CN1C1=CC=C(C(CN(C)C2)C=3SC4=CC=CC=C4C=3)C2=C1 HHHHRYUBBZKZLS-UHFFFAOYSA-N 0.000 claims description 2
- ZRXUBWRDOKMUIN-UHFFFAOYSA-N 4-[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1N1CCOCC1 ZRXUBWRDOKMUIN-UHFFFAOYSA-N 0.000 claims description 2
- SANFQQICYGPCNE-UHFFFAOYSA-N 4-[4-(1-benzothiophen-2-yl)-6-fluoro-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC(F)=C1N1CCOCC1 SANFQQICYGPCNE-UHFFFAOYSA-N 0.000 claims description 2
- IKPWOWMBLUCQJK-UHFFFAOYSA-N 4-[4-(1-benzothiophen-2-yl)-8-fluoro-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound FC1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1N1CCOCC1 IKPWOWMBLUCQJK-UHFFFAOYSA-N 0.000 claims description 2
- XHXPEBUSOLWQHY-UHFFFAOYSA-N 4-[4-(1-benzothiophen-3-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C4=CC=CC=C4SC=3)C2=CC=C1N1CCOCC1 XHXPEBUSOLWQHY-UHFFFAOYSA-N 0.000 claims description 2
- CYSAPVWWEXGZRU-UHFFFAOYSA-N 4-[4-(1-benzothiophen-4-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=4C=CSC=4C=CC=3)C2=CC=C1N1CCOCC1 CYSAPVWWEXGZRU-UHFFFAOYSA-N 0.000 claims description 2
- AUKIREGIIVMPAT-UHFFFAOYSA-N 4-[4-(4-fluoro-1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC(F)=C4C=3)C2=CC=C1N1CCOCC1 AUKIREGIIVMPAT-UHFFFAOYSA-N 0.000 claims description 2
- NYPSDRIEZWDXBQ-UHFFFAOYSA-N 4-[4-(6-fluoro-1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3SC4=CC(F)=CC=C4C=3)C2=CC=C1N1CCOCC1 NYPSDRIEZWDXBQ-UHFFFAOYSA-N 0.000 claims description 2
- KZZSQMZLYFWVJG-UHFFFAOYSA-N 6-[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]pyridazin-3-amine Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1C1=CC=C(N)N=N1 KZZSQMZLYFWVJG-UHFFFAOYSA-N 0.000 claims description 2
- HDQGFWFHAVLXBW-UHFFFAOYSA-N 6-[4-(1-benzothiophen-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n,n-dimethylpyridazin-3-amine Chemical compound N1=NC(N(C)C)=CC=C1C1=CC=C(C(CN(C)C2)C=3C=C4C=CSC4=CC=3)C2=C1 HDQGFWFHAVLXBW-UHFFFAOYSA-N 0.000 claims description 2
- NLCKXYLZJDCXEW-UHFFFAOYSA-N 7-[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]quinazoline Chemical compound C1=NC=NC2=CC(C3=CC=C4C(C=5SC6=CC=CC=C6C=5)CN(CC4=C3)C)=CC=C21 NLCKXYLZJDCXEW-UHFFFAOYSA-N 0.000 claims description 2
- 206010012335 Dependence Diseases 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 229960003920 cocaine Drugs 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 2
- 201000003631 narcolepsy Diseases 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 208000019906 panic disease Diseases 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000005545 phthalimidyl group Chemical group 0.000 claims description 2
- 230000035945 sensitivity Effects 0.000 claims description 2
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 90
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims 23
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 22
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 15
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 9
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 5
- 208000020925 Bipolar disease Diseases 0.000 claims 4
- UHEOSCFYXMSUPR-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-8-ol Chemical compound C1CNCC2=C1C=CC=C2O UHEOSCFYXMSUPR-UHFFFAOYSA-N 0.000 claims 3
- 208000001640 Fibromyalgia Diseases 0.000 claims 3
- 206010041250 Social phobia Diseases 0.000 claims 3
- 208000024714 major depressive disease Diseases 0.000 claims 3
- 208000004296 neuralgia Diseases 0.000 claims 3
- 208000021722 neuropathic pain Diseases 0.000 claims 3
- 230000001331 thermoregulatory effect Effects 0.000 claims 3
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 2
- XYYUSMIOLBNTRM-UHFFFAOYSA-N 1-pyridin-2-yl-1,2,3,4-tetrahydroisoquinoline Chemical compound N1CCC2=CC=CC=C2C1C1=CC=CC=N1 XYYUSMIOLBNTRM-UHFFFAOYSA-N 0.000 claims 2
- DVXVLDCHYMNAPW-UHFFFAOYSA-N 2-[4-(1h-indazol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-1,3-thiazole Chemical compound C1=C2CN(C)CC(C=3C=C4NN=CC4=CC=3)C2=CC=C1C1=NC=CS1 DVXVLDCHYMNAPW-UHFFFAOYSA-N 0.000 claims 2
- WKRHIRZCLIPXFQ-UHFFFAOYSA-N 2-methyl-4-(1-methylindazol-6-yl)-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4N(C)N=CC4=CC=3)C2=CC=C1C1=CC=CN=N1 WKRHIRZCLIPXFQ-UHFFFAOYSA-N 0.000 claims 2
- IZOUZIBSVMCGRD-UHFFFAOYSA-N 4-(1-benzylindol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C(C=C1C=C2)=CC=C1N2CC1=CC=CC=C1 IZOUZIBSVMCGRD-UHFFFAOYSA-N 0.000 claims 2
- LZAXXMDVJFRUHD-UHFFFAOYSA-N 4-(1h-indazol-5-yl)-2-methyl-7-morpholin-4-yl-1,3-dihydroisoquinolin-4-ol Chemical compound C=1C=C2C(O)(C=3C=C4C=NNC4=CC=3)CN(C)CC2=CC=1N1CCOCC1 LZAXXMDVJFRUHD-UHFFFAOYSA-N 0.000 claims 2
- STGGWYHRFXXNNC-UHFFFAOYSA-N 4-(1h-indazol-6-yl)-1,2-dimethyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2C(C)N(C)CC1C1=CC=C(C=NN2)C2=C1 STGGWYHRFXXNNC-UHFFFAOYSA-N 0.000 claims 2
- BUUFAPTZLPQVNR-UHFFFAOYSA-N 4-(1h-indazol-6-yl)-2-methyl-7-(6-methylpyridazin-3-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4NN=CC4=CC=3)C2=CC=C1C1=CC=C(C)N=N1 BUUFAPTZLPQVNR-UHFFFAOYSA-N 0.000 claims 2
- BVPFIPGKLSBXBZ-UHFFFAOYSA-N 4-(1h-indazol-6-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4NN=CC4=CC=3)C2=CC=C1C1=CC=CN=N1 BVPFIPGKLSBXBZ-UHFFFAOYSA-N 0.000 claims 2
- ICLYIZYYDUEQPQ-UHFFFAOYSA-N 4-(1h-indazol-6-yl)-2-methyl-7-pyridazin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4NN=CC4=CC=3)C2=CC=C1C1=CC=NN=C1 ICLYIZYYDUEQPQ-UHFFFAOYSA-N 0.000 claims 2
- LVKFCGXVTUCBBW-UHFFFAOYSA-N 4-(1h-indazol-6-yl)-2-methyl-7-pyrimidin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4NN=CC4=CC=3)C2=CC=C1C1=NC=CC=N1 LVKFCGXVTUCBBW-UHFFFAOYSA-N 0.000 claims 2
- WPSPEPVWMNEIJJ-UHFFFAOYSA-N 4-(1h-indazol-6-yl)-2-methyl-7-pyrimidin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4NN=CC4=CC=3)C2=CC=C1C1=CC=NC=N1 WPSPEPVWMNEIJJ-UHFFFAOYSA-N 0.000 claims 2
- SAWHLMKAORFAKB-UHFFFAOYSA-N 4-(1h-indazol-6-yl)-2-methyl-7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4NN=CC4=CC=3)C2=CC=C1C1=CN=CN=C1 SAWHLMKAORFAKB-UHFFFAOYSA-N 0.000 claims 2
- NFCDWUCZLVSLBB-UHFFFAOYSA-N 4-(7-fluoro-1h-indazol-6-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C(=C4NN=CC4=CC=3)F)C2=CC=C1C1=CC=CN=N1 NFCDWUCZLVSLBB-UHFFFAOYSA-N 0.000 claims 2
- BXPSINOKVAPRPV-UHFFFAOYSA-N 4-[2-[4-(1h-indazol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]propan-2-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=NNC4=CC=3)C2=CC=C1C(C)(C)N1CCOCC1 BXPSINOKVAPRPV-UHFFFAOYSA-N 0.000 claims 2
- AXQPLDLSQXCSCV-UHFFFAOYSA-N 4-[2-ethyl-8-fluoro-4-(1h-indazol-5-yl)-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound FC1=C2CN(CC)CC(C=3C=C4C=NNC4=CC=3)C2=CC=C1N1CCOCC1 AXQPLDLSQXCSCV-UHFFFAOYSA-N 0.000 claims 2
- NAAJJKWICIMSCL-UHFFFAOYSA-N 4-[4-(1h-indazol-5-yl)-8-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound COC1=C2CN(C)CC(C=3C=C4C=NNC4=CC=3)C2=CC=C1N1CCOCC1 NAAJJKWICIMSCL-UHFFFAOYSA-N 0.000 claims 2
- KWXVOKCVUNWADP-UHFFFAOYSA-N 4-[4-(1h-indazol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-3,5-dimethyl-1,2-oxazole Chemical compound C1=C2CN(C)CC(C=3C=C4NN=CC4=CC=3)C2=CC=C1C=1C(C)=NOC=1C KWXVOKCVUNWADP-UHFFFAOYSA-N 0.000 claims 2
- BPYJGTHULJOULH-UHFFFAOYSA-N 4-[6-fluoro-4-(1h-indazol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=NNC4=CC=3)C2=CC(F)=C1N1CCOCC1 BPYJGTHULJOULH-UHFFFAOYSA-N 0.000 claims 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- RLSNTIZLPLUYCU-UHFFFAOYSA-N 7-fluoro-4-(1h-indazol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=C(F)C=C2CN(C)CC1C1=CC=C(C=NN2)C2=C1 RLSNTIZLPLUYCU-UHFFFAOYSA-N 0.000 claims 2
- 208000030814 Eating disease Diseases 0.000 claims 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 2
- 208000011688 Generalised anxiety disease Diseases 0.000 claims 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 2
- 208000008930 Low Back Pain Diseases 0.000 claims 2
- 208000016285 Movement disease Diseases 0.000 claims 2
- 208000027030 Premenstrual dysphoric disease Diseases 0.000 claims 2
- 206010037180 Psychiatric symptoms Diseases 0.000 claims 2
- 208000005793 Restless legs syndrome Diseases 0.000 claims 2
- 201000001880 Sexual dysfunction Diseases 0.000 claims 2
- 208000022890 Sleep-related eating disease Diseases 0.000 claims 2
- 206010046543 Urinary incontinence Diseases 0.000 claims 2
- 235000014632 disordered eating Nutrition 0.000 claims 2
- 208000029364 generalized anxiety disease Diseases 0.000 claims 2
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 2
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 2
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims 2
- 229940044551 receptor antagonist Drugs 0.000 claims 2
- 239000002464 receptor antagonist Substances 0.000 claims 2
- 231100000872 sexual dysfunction Toxicity 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- OMZHCCXUVSEGAD-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-5-ol Chemical compound C1NCCC2=C1C=CC=C2O OMZHCCXUVSEGAD-UHFFFAOYSA-N 0.000 claims 1
- DKOMDMNIVULWFH-UHFFFAOYSA-N 1,2-dimethyl-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2C(C)N(C)CC1C1=CC=C(C=CC=C2)C2=C1 DKOMDMNIVULWFH-UHFFFAOYSA-N 0.000 claims 1
- DBPNAPNWMAMKEE-UHFFFAOYSA-N 1,2-dimethyl-4-naphthalen-2-yl-7-piperidin-1-yl-3,4-dihydro-1H-isoquinoline Chemical compound CN1C(C2=CC(=CC=C2C(C1)C1=CC2=CC=CC=C2C=C1)N1CCCCC1)C DBPNAPNWMAMKEE-UHFFFAOYSA-N 0.000 claims 1
- ZTHMDOYAWADNCF-UHFFFAOYSA-N 1-[4-(1-benzofuran-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n-methylmethanamine Chemical compound C1=CC=C2OC(C3C4=CC=C(C=C4CN(C)C3)CNC)=CC2=C1 ZTHMDOYAWADNCF-UHFFFAOYSA-N 0.000 claims 1
- ZQBHQOQHKNSXPI-UHFFFAOYSA-N 1-[4-(1-benzofuran-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n-methylcyclopropan-1-amine Chemical compound C=1C=C2C(C=3C=C4C=COC4=CC=3)CN(C)CC2=CC=1C1(NC)CC1 ZQBHQOQHKNSXPI-UHFFFAOYSA-N 0.000 claims 1
- DOGVXMKKFNXSFP-UHFFFAOYSA-N 1-[4-(1-benzofuran-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]pyridin-2-one Chemical compound C1=C2CN(C)CC(C=3C=C4C=COC4=CC=3)C2=CC=C1N1C=CC=CC1=O DOGVXMKKFNXSFP-UHFFFAOYSA-N 0.000 claims 1
- MUAACVMBOPKQEQ-UHFFFAOYSA-N 1-[4-(1-benzofuran-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n-methylmethanamine Chemical compound C1=C2C=COC2=CC(C2C3=CC=C(C=C3CN(C)C2)CNC)=C1 MUAACVMBOPKQEQ-UHFFFAOYSA-N 0.000 claims 1
- DUWJNXNJSGZZJW-UHFFFAOYSA-N 1-[4-(1-benzofuran-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]cyclopropan-1-amine Chemical compound C1=C2CN(C)CC(C=3C=C4OC=CC4=CC=3)C2=CC=C1C1(N)CC1 DUWJNXNJSGZZJW-UHFFFAOYSA-N 0.000 claims 1
- SIINQRWLIVVYKL-UHFFFAOYSA-N 1-[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n,n-dimethylmethanamine Chemical compound C1=CC=C2SC(C3C4=CC=C(C=C4CN(C)C3)CN(C)C)=CC2=C1 SIINQRWLIVVYKL-UHFFFAOYSA-N 0.000 claims 1
- XDEMDFGDTITBQU-UHFFFAOYSA-N 1-[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n-methylcyclopropan-1-amine Chemical compound C=1C=C2C(C=3SC4=CC=CC=C4C=3)CN(C)CC2=CC=1C1(NC)CC1 XDEMDFGDTITBQU-UHFFFAOYSA-N 0.000 claims 1
- LTVMXVCPOLJOEI-UHFFFAOYSA-N 1-[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n-methylmethanamine Chemical compound C1=CC=C2SC(C3C4=CC=C(C=C4CN(C)C3)CNC)=CC2=C1 LTVMXVCPOLJOEI-UHFFFAOYSA-N 0.000 claims 1
- BDLAKWIEWPJWSY-UHFFFAOYSA-N 1-[4-(1-benzothiophen-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n,n-dimethylmethanamine Chemical compound C1=C2SC=CC2=CC(C2C3=CC=C(C=C3CN(C)C2)CN(C)C)=C1 BDLAKWIEWPJWSY-UHFFFAOYSA-N 0.000 claims 1
- PQRWPAVPCOGQKI-UHFFFAOYSA-N 1-[4-(1-benzothiophen-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n-methylmethanamine Chemical compound C1=C2SC=CC2=CC(C2C3=CC=C(C=C3CN(C)C2)CNC)=C1 PQRWPAVPCOGQKI-UHFFFAOYSA-N 0.000 claims 1
- WSUSLONHQFOGQY-UHFFFAOYSA-N 1-[4-(1-benzothiophen-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n,n-dimethylmethanamine Chemical compound C1=C2C=CSC2=CC(C2C3=CC=C(C=C3CN(C)C2)CN(C)C)=C1 WSUSLONHQFOGQY-UHFFFAOYSA-N 0.000 claims 1
- SGIYURKTYUIVHE-UHFFFAOYSA-N 1-[4-(1-benzothiophen-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n-methylcyclopropan-1-amine Chemical compound C=1C=C2C(C=3C=C4SC=CC4=CC=3)CN(C)CC2=CC=1C1(NC)CC1 SGIYURKTYUIVHE-UHFFFAOYSA-N 0.000 claims 1
- ZJUAPQZBEJZJIT-UHFFFAOYSA-N 1-[4-(1-benzothiophen-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n-methylmethanamine Chemical compound C1=C2C=CSC2=CC(C2C3=CC=C(C=C3CN(C)C2)CNC)=C1 ZJUAPQZBEJZJIT-UHFFFAOYSA-N 0.000 claims 1
- YZXYPOPBFINJEX-UHFFFAOYSA-N 1-[4-(1-benzothiophen-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]cyclopropan-1-amine Chemical compound C1=C2CN(C)CC(C=3C=C4SC=CC4=CC=3)C2=CC=C1C1(N)CC1 YZXYPOPBFINJEX-UHFFFAOYSA-N 0.000 claims 1
- GMSPBUCPAIYKDP-UHFFFAOYSA-N 1-[4-(1-benzothiophen-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]pyridin-2-one Chemical compound C1=C2CN(C)CC(C=3C=C4SC=CC4=CC=3)C2=CC=C1N1C=CC=CC1=O GMSPBUCPAIYKDP-UHFFFAOYSA-N 0.000 claims 1
- QDDZOAVPVIPGCA-UHFFFAOYSA-N 1-[4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n,n-dimethylmethanamine Chemical compound C1=CC=C2NC(C3C4=CC=C(C=C4CN(C)C3)CN(C)C)=CC2=C1 QDDZOAVPVIPGCA-UHFFFAOYSA-N 0.000 claims 1
- WESSXYNDMAMDHN-UHFFFAOYSA-N 1-[4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n-methylcyclopropan-1-amine Chemical compound C=1C=C2C(C=3NC4=CC=CC=C4C=3)CN(C)CC2=CC=1C1(NC)CC1 WESSXYNDMAMDHN-UHFFFAOYSA-N 0.000 claims 1
- MCVFGRNTXSGLBJ-UHFFFAOYSA-N 1-[4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]cyclopropan-1-amine Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1C1(N)CC1 MCVFGRNTXSGLBJ-UHFFFAOYSA-N 0.000 claims 1
- YTOGMSZHJZGRBN-UHFFFAOYSA-N 1-[4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]phthalazine Chemical compound C1=CC=C2C(C3=CC=C4C(C=5NC6=CC=CC=C6C=5)CN(CC4=C3)C)=NN=CC2=C1 YTOGMSZHJZGRBN-UHFFFAOYSA-N 0.000 claims 1
- SBVQGTFLYSISPG-UHFFFAOYSA-N 1-[4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]pyridin-2-one Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1N1C=CC=CC1=O SBVQGTFLYSISPG-UHFFFAOYSA-N 0.000 claims 1
- GKLFHZPCKXPQLY-UHFFFAOYSA-N 1-[4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n,n-dimethylcyclopropan-1-amine Chemical compound C=1C=C2C(C=3C=C4C=CNC4=CC=3)CN(C)CC2=CC=1C1(N(C)C)CC1 GKLFHZPCKXPQLY-UHFFFAOYSA-N 0.000 claims 1
- RKOSHJRDQZLAKN-UHFFFAOYSA-N 1-[4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n-methylcyclopropan-1-amine Chemical compound C=1C=C2C(C=3C=C4C=CNC4=CC=3)CN(C)CC2=CC=1C1(NC)CC1 RKOSHJRDQZLAKN-UHFFFAOYSA-N 0.000 claims 1
- LMJWAUXFLLNEDC-UHFFFAOYSA-N 1-[4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n-methylmethanamine Chemical compound C1=C2NC=CC2=CC(C2C3=CC=C(C=C3CN(C)C2)CNC)=C1 LMJWAUXFLLNEDC-UHFFFAOYSA-N 0.000 claims 1
- XAUIPWUVWLMLNT-UHFFFAOYSA-N 1-[4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]pyridin-2-one Chemical compound C1=C2CN(C)CC(C=3C=C4C=CNC4=CC=3)C2=CC=C1N1C=CC=CC1=O XAUIPWUVWLMLNT-UHFFFAOYSA-N 0.000 claims 1
- RUGFDQXLFWQFQE-UHFFFAOYSA-N 1-[4-(1h-indol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n-methylmethanamine Chemical compound C1=C2C=CNC2=CC(C2C3=CC=C(C=C3CN(C)C2)CNC)=C1 RUGFDQXLFWQFQE-UHFFFAOYSA-N 0.000 claims 1
- XYMNEUYWZHMSJD-UHFFFAOYSA-N 1-pyridazin-4-yl-1,2,3,4-tetrahydroisoquinoline Chemical compound N1CCC2=CC=CC=C2C1C1=CC=NN=C1 XYMNEUYWZHMSJD-UHFFFAOYSA-N 0.000 claims 1
- PQUCZQQPRMLVLB-UHFFFAOYSA-N 1-pyridin-3-yl-1,2,3,4-tetrahydroisoquinoline Chemical compound N1CCC2=CC=CC=C2C1C1=CC=CN=C1 PQUCZQQPRMLVLB-UHFFFAOYSA-N 0.000 claims 1
- DAHSGAUUVRFWQR-UHFFFAOYSA-N 1-pyrimidin-2-yl-1,2,3,4-tetrahydroisoquinoline Chemical compound N1CCC2=CC=CC=C2C1C1=NC=CC=N1 DAHSGAUUVRFWQR-UHFFFAOYSA-N 0.000 claims 1
- HRKRXAYVLLJWDH-UHFFFAOYSA-N 2,4-dimethyl-4-naphthalen-2-yl-1,3-dihydroisoquinoline Chemical compound C1=CC=CC2=CC(C3(C)C4=CC=CC=C4CN(C3)C)=CC=C21 HRKRXAYVLLJWDH-UHFFFAOYSA-N 0.000 claims 1
- JSHASAWQPDVBRE-UHFFFAOYSA-N 2,5-dimethyl-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C12=C(C)C=CC=C2CN(C)CC1C1=CC=C(C=CC=C2)C2=C1 JSHASAWQPDVBRE-UHFFFAOYSA-N 0.000 claims 1
- BQKFYURDSXPYJM-UHFFFAOYSA-N 2,7-dimethyl-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=C(C)C=C2CN(C)CC1C1=CC=C(C=CC=C2)C2=C1 BQKFYURDSXPYJM-UHFFFAOYSA-N 0.000 claims 1
- FYLBXIXYOYZXOE-UHFFFAOYSA-N 2,8-dimethyl-4-naphthalen-2-yl-7-pyrimidin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound CC1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=NC=CC=N1 FYLBXIXYOYZXOE-UHFFFAOYSA-N 0.000 claims 1
- SZPQHXPHTVFABM-UHFFFAOYSA-N 2,8-dimethyl-4-naphthalen-2-yl-7-pyrimidin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound CC1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=CC=NC=N1 SZPQHXPHTVFABM-UHFFFAOYSA-N 0.000 claims 1
- OEEWLJPHFBXNLS-UHFFFAOYSA-N 2,8-dimethyl-4-naphthalen-2-yl-7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinoline Chemical compound CC1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=CN=CN=C1 OEEWLJPHFBXNLS-UHFFFAOYSA-N 0.000 claims 1
- MEZRFQQYDJKZGO-UHFFFAOYSA-N 2-(2-methyl-1-morpholin-4-yl-3,4-dihydro-1h-isoquinolin-4-yl)-1,3-benzoxazole Chemical compound CN1CC(C=2OC3=CC=CC=C3N=2)C2=CC=CC=C2C1N1CCOCC1 MEZRFQQYDJKZGO-UHFFFAOYSA-N 0.000 claims 1
- NKPPXYSAEFOLTJ-UHFFFAOYSA-N 2-(2-methyl-1-piperidin-1-yl-3,4-dihydro-1h-isoquinolin-4-yl)-1,3-benzothiazole Chemical compound CN1CC(C=2SC3=CC=CC=C3N=2)C2=CC=CC=C2C1N1CCCCC1 NKPPXYSAEFOLTJ-UHFFFAOYSA-N 0.000 claims 1
- ITRJZUMWUPZGID-UHFFFAOYSA-N 2-(2-methyl-1-piperidin-1-yl-3,4-dihydro-1h-isoquinolin-4-yl)-1,3-benzoxazole Chemical compound CN1CC(C=2OC3=CC=CC=C3N=2)C2=CC=CC=C2C1N1CCCCC1 ITRJZUMWUPZGID-UHFFFAOYSA-N 0.000 claims 1
- QZDHFCQRUJAJLC-UHFFFAOYSA-N 2-(2-methyl-1-pyrrolidin-1-yl-3,4-dihydro-1h-isoquinolin-4-yl)-1,3-benzothiazole Chemical compound CN1CC(C=2SC3=CC=CC=C3N=2)C2=CC=CC=C2C1N1CCCC1 QZDHFCQRUJAJLC-UHFFFAOYSA-N 0.000 claims 1
- ZVDSWRLGKOSCTR-UHFFFAOYSA-N 2-(2-methyl-1-pyrrolidin-1-yl-3,4-dihydro-1h-isoquinolin-4-yl)-1,3-benzoxazole Chemical compound CN1CC(C=2OC3=CC=CC=C3N=2)C2=CC=CC=C2C1N1CCCC1 ZVDSWRLGKOSCTR-UHFFFAOYSA-N 0.000 claims 1
- VKOXAWMIVMBFGK-UHFFFAOYSA-N 2-(2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)quinazoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=NC=C(C=CC=C2)C2=N1 VKOXAWMIVMBFGK-UHFFFAOYSA-N 0.000 claims 1
- FPUVXXNHNRGOQY-UHFFFAOYSA-N 2-(2-methyl-7-piperidin-1-yl-3,4-dihydro-1h-isoquinolin-4-yl)thieno[2,3-b]pyridine Chemical compound C1=C2CN(C)CC(C=3SC4=NC=CC=C4C=3)C2=CC=C1N1CCCCC1 FPUVXXNHNRGOQY-UHFFFAOYSA-N 0.000 claims 1
- KEDXOEAATAPWLQ-UHFFFAOYSA-N 2-(2-methyl-7-piperidin-1-yl-3,4-dihydro-1h-isoquinolin-4-yl)thieno[3,2-b]pyridine Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CN=C4C=3)C2=CC=C1N1CCCCC1 KEDXOEAATAPWLQ-UHFFFAOYSA-N 0.000 claims 1
- UIDMYHSOIGOQGX-UHFFFAOYSA-N 2-(2-methyl-7-pyrrolidin-1-yl-3,4-dihydro-1h-isoquinolin-4-yl)thieno[2,3-b]pyridine Chemical compound C1=C2CN(C)CC(C=3SC4=NC=CC=C4C=3)C2=CC=C1N1CCCC1 UIDMYHSOIGOQGX-UHFFFAOYSA-N 0.000 claims 1
- ALHSFNSWDFQLFC-UHFFFAOYSA-N 2-[4-(1-benzofuran-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound N1=C2C=CC=CN2C(=O)N1C1=CC=C2C(C=3C=C4C=COC4=CC=3)CN(C)CC2=C1 ALHSFNSWDFQLFC-UHFFFAOYSA-N 0.000 claims 1
- CHUGUVOALHCBKT-UHFFFAOYSA-N 2-[4-(1-benzofuran-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-5-methyl-1,3-thiazole Chemical compound C1=C2CN(C)CC(C=3C=C4OC=CC4=CC=3)C2=CC=C1C1=NC=C(C)S1 CHUGUVOALHCBKT-UHFFFAOYSA-N 0.000 claims 1
- ALWNDVBHEWUFDN-UHFFFAOYSA-N 2-[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n,n-dimethylpropan-2-amine Chemical compound C1=CC=C2SC(C3C4=CC=C(C=C4CN(C)C3)C(C)(C)N(C)C)=CC2=C1 ALWNDVBHEWUFDN-UHFFFAOYSA-N 0.000 claims 1
- JTZCZUKRAQQIEE-UHFFFAOYSA-N 2-[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]quinazoline Chemical compound C1=CC=CC2=NC(C3=CC=C4C(C=5SC6=CC=CC=C6C=5)CN(CC4=C3)C)=NC=C21 JTZCZUKRAQQIEE-UHFFFAOYSA-N 0.000 claims 1
- XQZRLSMKHQKJCT-UHFFFAOYSA-N 2-[4-(1-benzothiophen-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-1,3-thiazole Chemical compound C1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=NC=CS1 XQZRLSMKHQKJCT-UHFFFAOYSA-N 0.000 claims 1
- SPMYEIAYXQXPIR-UHFFFAOYSA-N 2-[4-(1-benzothiophen-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n,n-dimethylpropan-2-amine Chemical compound C1=C2SC=CC2=CC(C2C3=CC=C(C=C3CN(C)C2)C(C)(C)N(C)C)=C1 SPMYEIAYXQXPIR-UHFFFAOYSA-N 0.000 claims 1
- FHGFBQODKPVGDU-UHFFFAOYSA-N 2-[4-(1-benzothiophen-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]quinazoline Chemical compound C1=CC=CC2=NC(C3=CC=C4C(C=5C=C6C=CSC6=CC=5)CN(CC4=C3)C)=NC=C21 FHGFBQODKPVGDU-UHFFFAOYSA-N 0.000 claims 1
- YKDDRFJWPJGVFD-UHFFFAOYSA-N 2-[4-(1-benzothiophen-5-yl)-3,4-dihydro-1h-isoquinolin-2-yl]-n,n-dimethylethanamine Chemical compound C12=CC=CC=C2CN(CCN(C)C)CC1C1=CC=C(SC=C2)C2=C1 YKDDRFJWPJGVFD-UHFFFAOYSA-N 0.000 claims 1
- IYNFMNFMDOBZCA-UHFFFAOYSA-N 2-[4-(1-benzothiophen-5-yl)-3,4-dihydro-1h-isoquinolin-2-yl]acetonitrile Chemical compound C12=CC=CC=C2CN(CC#N)CC1C1=CC=C(SC=C2)C2=C1 IYNFMNFMDOBZCA-UHFFFAOYSA-N 0.000 claims 1
- CLXWFGNHOQXSLX-UHFFFAOYSA-N 2-[4-(1-benzothiophen-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-1,3-thiazole Chemical compound C1=C2CN(C)CC(C=3C=C4SC=CC4=CC=3)C2=CC=C1C1=NC=CS1 CLXWFGNHOQXSLX-UHFFFAOYSA-N 0.000 claims 1
- NFAVBSPRWOEENQ-UHFFFAOYSA-N 2-[4-(1-benzothiophen-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-5-methyl-1,3-thiazole Chemical compound C1=C2CN(C)CC(C=3C=C4SC=CC4=CC=3)C2=CC=C1C1=NC=C(C)S1 NFAVBSPRWOEENQ-UHFFFAOYSA-N 0.000 claims 1
- LMFBETVYHQSWBE-UHFFFAOYSA-N 2-[4-(1-benzothiophen-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n,n-dimethylpropan-2-amine Chemical compound C1=C2C=CSC2=CC(C2C3=CC=C(C=C3CN(C)C2)C(C)(C)N(C)C)=C1 LMFBETVYHQSWBE-UHFFFAOYSA-N 0.000 claims 1
- ZOEJLSKEPKNPEK-UHFFFAOYSA-N 2-[4-(1h-indazol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-1,3-thiazole Chemical compound C1=C2CN(C)CC(C=3C=C4C=NNC4=CC=3)C2=CC=C1C1=NC=CS1 ZOEJLSKEPKNPEK-UHFFFAOYSA-N 0.000 claims 1
- CMLPGAPYAHNVFB-UHFFFAOYSA-N 2-[4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-1,3-thiazole Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1C1=NC=CS1 CMLPGAPYAHNVFB-UHFFFAOYSA-N 0.000 claims 1
- BBCVHLRETAUERC-UHFFFAOYSA-N 2-[4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-5-methyl-1,3-thiazole Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1C1=NC=C(C)S1 BBCVHLRETAUERC-UHFFFAOYSA-N 0.000 claims 1
- AMPSYYSQSZLAFR-UHFFFAOYSA-N 2-[4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]quinoxaline Chemical compound C1=CC=CC2=NC(C3=CC=C4C(C=5NC6=CC=CC=C6C=5)CN(CC4=C3)C)=CN=C21 AMPSYYSQSZLAFR-UHFFFAOYSA-N 0.000 claims 1
- XRJSPHCQZVRXTA-UHFFFAOYSA-N 2-[4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-1,3-thiazole Chemical compound C1=C2CN(C)CC(C=3C=C4C=CNC4=CC=3)C2=CC=C1C1=NC=CS1 XRJSPHCQZVRXTA-UHFFFAOYSA-N 0.000 claims 1
- GVSADXKMKJEXPS-UHFFFAOYSA-N 2-[4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-5-methyl-1,3-thiazole Chemical compound C1=C2CN(C)CC(C=3C=C4C=CNC4=CC=3)C2=CC=C1C1=NC=C(C)S1 GVSADXKMKJEXPS-UHFFFAOYSA-N 0.000 claims 1
- YEPDVKGCJDOYJE-UHFFFAOYSA-N 2-[4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]quinoxaline Chemical compound C1=CC=CC2=NC(C3=CC=C4C(C=5C=C6C=CNC6=CC=5)CN(CC4=C3)C)=CN=C21 YEPDVKGCJDOYJE-UHFFFAOYSA-N 0.000 claims 1
- BMOZPKPAXNEOOC-UHFFFAOYSA-N 2-[4-(1h-indol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-1,3-thiazole Chemical compound C1=C2CN(C)CC(C=3C=C4NC=CC4=CC=3)C2=CC=C1C1=NC=CS1 BMOZPKPAXNEOOC-UHFFFAOYSA-N 0.000 claims 1
- FRGXVGPQHFDNOE-UHFFFAOYSA-N 2-[4-(1h-indol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-5-methyl-1,3-thiazole Chemical compound C1=C2CN(C)CC(C=3C=C4NC=CC4=CC=3)C2=CC=C1C1=NC=C(C)S1 FRGXVGPQHFDNOE-UHFFFAOYSA-N 0.000 claims 1
- MDAJCVVJQUSLJH-UHFFFAOYSA-N 2-[4-(1h-indol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]propan-2-amine Chemical compound C12=CC=C(C(C)(C)N)C=C2CN(C)CC1C1=CC=C(C=CN2)C2=C1 MDAJCVVJQUSLJH-UHFFFAOYSA-N 0.000 claims 1
- WCHGCJJYOTVFDR-UHFFFAOYSA-N 2-ethyl-4-(1h-indazol-5-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(CC)CC1C1=CC=C(NN=C2)C2=C1 WCHGCJJYOTVFDR-UHFFFAOYSA-N 0.000 claims 1
- BWSSTPFWOOGFHV-UHFFFAOYSA-N 2-ethyl-4-(1h-indazol-5-yl)-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(CC)CC(C=3C=C4C=NNC4=CC=3)C2=CC=C1C1=CC=CN=N1 BWSSTPFWOOGFHV-UHFFFAOYSA-N 0.000 claims 1
- AWPMGTSMDULQAT-UHFFFAOYSA-N 2-ethyl-4-(1h-indazol-6-yl)-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(CC)CC(C=3C=C4NN=CC4=CC=3)C2=CC=C1C1=CC=CN=N1 AWPMGTSMDULQAT-UHFFFAOYSA-N 0.000 claims 1
- IACVFFMWZYMYJM-UHFFFAOYSA-N 2-ethyl-4-(1h-indol-6-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(CC)CC1C1=CC=C(C=CN2)C2=C1 IACVFFMWZYMYJM-UHFFFAOYSA-N 0.000 claims 1
- PPZKULZKFSDVCS-UHFFFAOYSA-N 2-ethyl-4-(7-methoxy-1-benzothiophen-6-yl)-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(CC)CC(C=3C(=C4SC=CC4=CC=3)OC)C2=CC=C1C1=CC=CN=N1 PPZKULZKFSDVCS-UHFFFAOYSA-N 0.000 claims 1
- CENMESGDNXJNDZ-UHFFFAOYSA-N 2-ethyl-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(CC)CC1C1=CC=C(C=CC=C2)C2=C1 CENMESGDNXJNDZ-UHFFFAOYSA-N 0.000 claims 1
- JYROMKQFSCRAIU-UHFFFAOYSA-N 2-ethyl-4-naphthalen-2-yl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(CC)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=CC=CN=N1 JYROMKQFSCRAIU-UHFFFAOYSA-N 0.000 claims 1
- QFRZKMRLGKPNDP-UHFFFAOYSA-N 2-ethyl-8-fluoro-4-(1-methylindol-5-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC(F)=C2CN(CC)CC1C1=CC=C(N(C)C=C2)C2=C1 QFRZKMRLGKPNDP-UHFFFAOYSA-N 0.000 claims 1
- SVWMEKHHENQIGU-UHFFFAOYSA-N 2-ethyl-8-fluoro-4-(1-methylindol-6-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC(F)=C2CN(CC)CC1C1=CC=C(C=CN2C)C2=C1 SVWMEKHHENQIGU-UHFFFAOYSA-N 0.000 claims 1
- WCYUVKNDLJNXBA-UHFFFAOYSA-N 2-ethyl-8-fluoro-4-(1h-indazol-5-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC(F)=C2CN(CC)CC1C1=CC=C(NN=C2)C2=C1 WCYUVKNDLJNXBA-UHFFFAOYSA-N 0.000 claims 1
- RCJFIDPLEAVYQD-UHFFFAOYSA-N 2-ethyl-8-fluoro-4-(7-methoxy-1-benzothiophen-6-yl)-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(CC)CC(C=3C(=C4SC=CC4=CC=3)OC)C2=CC=C1C1=CC=CN=N1 RCJFIDPLEAVYQD-UHFFFAOYSA-N 0.000 claims 1
- KOINWPBHZJMUQK-UHFFFAOYSA-N 2-ethyl-8-fluoro-4-naphthalen-2-yl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(CC)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=CC=CN=N1 KOINWPBHZJMUQK-UHFFFAOYSA-N 0.000 claims 1
- YPOWILWYYQHNJB-UHFFFAOYSA-N 2-methyl-4-(1-methylindol-2-yl)-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3N(C4=CC=CC=C4C=3)C)C2=CC=C1C1=CC=CN=N1 YPOWILWYYQHNJB-UHFFFAOYSA-N 0.000 claims 1
- TWBQIFJKOMOFPD-UHFFFAOYSA-N 2-methyl-4-(1-methylindol-5-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=C(N(C)C=C2)C2=C1 TWBQIFJKOMOFPD-UHFFFAOYSA-N 0.000 claims 1
- PYMPOPVOCIUCLC-UHFFFAOYSA-N 2-methyl-4-(1-methylindol-6-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=C(C=CN2C)C2=C1 PYMPOPVOCIUCLC-UHFFFAOYSA-N 0.000 claims 1
- ORGLMMURYZTPPP-UHFFFAOYSA-N 2-methyl-4-(1-methylindol-6-yl)-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4N(C)C=CC4=CC=3)C2=CC=C1C1=CC=CN=N1 ORGLMMURYZTPPP-UHFFFAOYSA-N 0.000 claims 1
- HLRUEGUCIMLXDJ-UHFFFAOYSA-N 2-methyl-4-(1-methylnaphthalen-2-yl)-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C(=C4C=CC=CC4=CC=3)C)C2=CC=C1C1=CC=CN=N1 HLRUEGUCIMLXDJ-UHFFFAOYSA-N 0.000 claims 1
- SEVFTNQKUDMZDO-UHFFFAOYSA-N 2-methyl-4-(2-methyl-1-benzothiophen-5-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=C(SC(C)=C2)C2=C1 SEVFTNQKUDMZDO-UHFFFAOYSA-N 0.000 claims 1
- QRYQHDYLDXXMLF-UHFFFAOYSA-N 2-methyl-4-(2-methyl-1-benzothiophen-6-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=C(C=C(C)S2)C2=C1 QRYQHDYLDXXMLF-UHFFFAOYSA-N 0.000 claims 1
- MTSSBXBWOGKUHN-UHFFFAOYSA-N 2-methyl-4-(3-methyl-1-benzofuran-5-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=C(OC=C2C)C2=C1 MTSSBXBWOGKUHN-UHFFFAOYSA-N 0.000 claims 1
- BLIBIXZYYJSZAU-UHFFFAOYSA-N 2-methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=C(CCCC2)C2=C1 BLIBIXZYYJSZAU-UHFFFAOYSA-N 0.000 claims 1
- APYUNIKBJXFYBO-UHFFFAOYSA-N 2-methyl-4-(5-methylnaphthalen-2-yl)-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=C(C)C4=CC=3)C2=CC=C1C1=CC=CN=N1 APYUNIKBJXFYBO-UHFFFAOYSA-N 0.000 claims 1
- VRKYDANQLWBYKU-UHFFFAOYSA-N 2-methyl-4-(6-methylsulfonylnaphthalen-2-yl)-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC(=CC4=CC=3)S(C)(=O)=O)C2=CC=C1C1=CC=CN=N1 VRKYDANQLWBYKU-UHFFFAOYSA-N 0.000 claims 1
- UWPMCMHCHLBSRJ-UHFFFAOYSA-N 2-methyl-4-(7-methyl-1h-indazol-5-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC(C)=C(NN=C2)C2=C1 UWPMCMHCHLBSRJ-UHFFFAOYSA-N 0.000 claims 1
- DXZCVHIIJMLZDN-UHFFFAOYSA-N 2-methyl-4-([1,2,4]triazolo[4,3-a]pyridin-7-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC2=NN=CN2C=C1 DXZCVHIIJMLZDN-UHFFFAOYSA-N 0.000 claims 1
- ZWXWSADDHIHLIF-UHFFFAOYSA-N 2-methyl-4-naphthalen-2-yl-1,3-dihydroisoquinolin-4-ol Chemical compound C1=CC=CC2=CC(C3(O)C4=CC=CC=C4CN(C3)C)=CC=C21 ZWXWSADDHIHLIF-UHFFFAOYSA-N 0.000 claims 1
- MIYHYMAELOAKGI-UHFFFAOYSA-N 2-methyl-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinolin-7-ol Chemical compound C12=CC=C(O)C=C2CN(C)CC1C1=CC=C(C=CC=C2)C2=C1 MIYHYMAELOAKGI-UHFFFAOYSA-N 0.000 claims 1
- VKFUPJSKOSFXMT-UHFFFAOYSA-N 2-methyl-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=C(C=CC=C2)C2=C1 VKFUPJSKOSFXMT-UHFFFAOYSA-N 0.000 claims 1
- SNMQJMKTFDHYKU-UHFFFAOYSA-N 2-methyl-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinoline-7-carbonitrile Chemical compound C12=CC=C(C#N)C=C2CN(C)CC1C1=CC=C(C=CC=C2)C2=C1 SNMQJMKTFDHYKU-UHFFFAOYSA-N 0.000 claims 1
- IQPAQAKZZDXSPR-UHFFFAOYSA-N 2-methyl-4-naphthalen-2-yl-7-[6-(trifluoromethyl)pyridazin-3-yl]-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=CC=C(C(F)(F)F)N=N1 IQPAQAKZZDXSPR-UHFFFAOYSA-N 0.000 claims 1
- LHIZBXGJZDUAEG-UHFFFAOYSA-N 2-methyl-4-naphthalen-2-yl-7-piperidin-1-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1N1CCCCC1 LHIZBXGJZDUAEG-UHFFFAOYSA-N 0.000 claims 1
- PXWNVSKWHXCKSK-UHFFFAOYSA-N 2-methyl-4-naphthalen-2-yl-7-pyrazin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=CN=CC=N1 PXWNVSKWHXCKSK-UHFFFAOYSA-N 0.000 claims 1
- ICZKDHZLUUVEOD-UHFFFAOYSA-N 2-methyl-4-naphthalen-2-yl-7-pyridazin-3-yl-3,4-dihydro-1H-isoquinolin-8-ol Chemical compound OC1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=CC=CN=N1 ICZKDHZLUUVEOD-UHFFFAOYSA-N 0.000 claims 1
- VLBMNJKZTDKZNF-UHFFFAOYSA-N 2-methyl-4-naphthalen-2-yl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=CC=CN=N1 VLBMNJKZTDKZNF-UHFFFAOYSA-N 0.000 claims 1
- FWSBFFOVNHIPEA-UHFFFAOYSA-N 2-methyl-4-naphthalen-2-yl-7-pyrimidin-2-yl-3,4-dihydro-1H-isoquinolin-8-ol Chemical compound OC1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=NC=CC=N1 FWSBFFOVNHIPEA-UHFFFAOYSA-N 0.000 claims 1
- JTRLJCABWVCWGM-UHFFFAOYSA-N 2-methyl-4-naphthalen-2-yl-7-pyrimidin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=NC=CC=N1 JTRLJCABWVCWGM-UHFFFAOYSA-N 0.000 claims 1
- FJRNTQYQUMEDMF-UHFFFAOYSA-N 2-methyl-4-naphthalen-2-yl-7-pyrimidin-4-yl-3,4-dihydro-1H-isoquinolin-8-ol Chemical compound OC1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=CC=NC=N1 FJRNTQYQUMEDMF-UHFFFAOYSA-N 0.000 claims 1
- GFNBJFXIJAGJTO-UHFFFAOYSA-N 2-methyl-4-naphthalen-2-yl-7-pyrimidin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=CC=NC=N1 GFNBJFXIJAGJTO-UHFFFAOYSA-N 0.000 claims 1
- WLLVDSYYZIHFSQ-UHFFFAOYSA-N 2-methyl-4-naphthalen-2-yl-7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinolin-8-ol Chemical compound OC1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=CN=CN=C1 WLLVDSYYZIHFSQ-UHFFFAOYSA-N 0.000 claims 1
- IKIOVKAFDWKFGP-UHFFFAOYSA-N 2-methyl-4-naphthalen-2-yl-7-pyrrolidin-1-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1N1CCCC1 IKIOVKAFDWKFGP-UHFFFAOYSA-N 0.000 claims 1
- APWKQUAMWZEUKK-UHFFFAOYSA-N 2-methyl-4-quinolin-6-yl-1,3-dihydroisoquinolin-4-ol Chemical compound N1=CC=CC2=CC(C3(O)C4=CC=CC=C4CN(C3)C)=CC=C21 APWKQUAMWZEUKK-UHFFFAOYSA-N 0.000 claims 1
- NROIWUZDYOPWTQ-UHFFFAOYSA-N 2-methyl-5-(2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)-1,3-benzoxazole Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=C(OC(C)=N2)C2=C1 NROIWUZDYOPWTQ-UHFFFAOYSA-N 0.000 claims 1
- JRQOKOMFKZBCAT-UHFFFAOYSA-N 2-methyl-6-(2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)-1,3-benzothiazole Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=C(N=C(C)S2)C2=C1 JRQOKOMFKZBCAT-UHFFFAOYSA-N 0.000 claims 1
- JQDLSTNVYUTNRY-UHFFFAOYSA-N 2-methyl-7-methylsulfonyl-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=C(S(C)(=O)=O)C=C2CN(C)CC1C1=CC=C(C=CC=C2)C2=C1 JQDLSTNVYUTNRY-UHFFFAOYSA-N 0.000 claims 1
- KPCBRXOVAMINFD-UHFFFAOYSA-N 2-methyl-7-piperidin-1-yl-4-([1,2,4]triazolo[4,3-a]pyridin-7-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C3=CC4=NN=CN4C=C3)C2=CC=C1N1CCCCC1 KPCBRXOVAMINFD-UHFFFAOYSA-N 0.000 claims 1
- KANGEHRWVVUULP-UHFFFAOYSA-N 2-methyl-7-piperidin-1-yl-4-pyrazolo[1,5-a]pyridin-5-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C3=CC4=CC=NN4C=C3)C2=CC=C1N1CCCCC1 KANGEHRWVVUULP-UHFFFAOYSA-N 0.000 claims 1
- DAVSFIRLNHWILW-UHFFFAOYSA-N 2-methyl-7-pyrazin-2-yl-4-[3-(trifluoromethyl)-1-benzothiophen-5-yl]-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C(=CSC4=CC=3)C(F)(F)F)C2=CC=C1C1=CN=CC=N1 DAVSFIRLNHWILW-UHFFFAOYSA-N 0.000 claims 1
- RNRVIEUZTBJYET-UHFFFAOYSA-N 2-methyl-7-pyrazin-2-yl-4-[3-(trifluoromethyl)-1-benzothiophen-6-yl]-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4SC=C(C4=CC=3)C(F)(F)F)C2=CC=C1C1=CN=CC=N1 RNRVIEUZTBJYET-UHFFFAOYSA-N 0.000 claims 1
- HHYZWBKRRTVPNM-UHFFFAOYSA-N 2-methyl-7-pyridazin-3-yl-4-[3-(trifluoromethyl)-1-benzothiophen-5-yl]-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C(=CSC4=CC=3)C(F)(F)F)C2=CC=C1C1=CC=CN=N1 HHYZWBKRRTVPNM-UHFFFAOYSA-N 0.000 claims 1
- NIOFXCSLOOQPQS-UHFFFAOYSA-N 2-methyl-7-pyridazin-3-yl-4-[3-(trifluoromethyl)-1-benzothiophen-6-yl]-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4SC=C(C4=CC=3)C(F)(F)F)C2=CC=C1C1=CC=CN=N1 NIOFXCSLOOQPQS-UHFFFAOYSA-N 0.000 claims 1
- AMAUOAQGLSJXJK-UHFFFAOYSA-N 2-methyl-7-pyrimidin-2-yl-4-[3-(trifluoromethyl)-1-benzothiophen-6-yl]-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4SC=C(C4=CC=3)C(F)(F)F)C2=CC=C1C1=NC=CC=N1 AMAUOAQGLSJXJK-UHFFFAOYSA-N 0.000 claims 1
- SZLSXTLHBXCHCZ-UHFFFAOYSA-N 2-methyl-7-pyrimidin-5-yl-4-[3-(trifluoromethyl)-1-benzothiophen-5-yl]-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C(=CSC4=CC=3)C(F)(F)F)C2=CC=C1C1=CN=CN=C1 SZLSXTLHBXCHCZ-UHFFFAOYSA-N 0.000 claims 1
- CMKIQNUEXQFGDG-UHFFFAOYSA-N 2-methyl-7-pyrimidin-5-yl-4-[3-(trifluoromethyl)-1-benzothiophen-6-yl]-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4SC=C(C4=CC=3)C(F)(F)F)C2=CC=C1C1=CN=CN=C1 CMKIQNUEXQFGDG-UHFFFAOYSA-N 0.000 claims 1
- FEURVVDNHHBHDG-UHFFFAOYSA-N 3,5-dimethyl-4-(2-methyl-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinolin-7-yl)-1,2-oxazole Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C=1C(C)=NOC=1C FEURVVDNHHBHDG-UHFFFAOYSA-N 0.000 claims 1
- KYCBSTZIUNRVLO-UHFFFAOYSA-N 3-(2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinolin-4-yl)naphthalene-2-carbonitrile Chemical compound C1=C2CN(C)CC(C=3C(=CC4=CC=CC=C4C=3)C#N)C2=CC=C1C1=CC=CN=N1 KYCBSTZIUNRVLO-UHFFFAOYSA-N 0.000 claims 1
- ABOQNJDBQHUXNW-UHFFFAOYSA-N 3-(trifluoromethyl)-1-benzothiophene Chemical compound C1=CC=C2C(C(F)(F)F)=CSC2=C1 ABOQNJDBQHUXNW-UHFFFAOYSA-N 0.000 claims 1
- UVOXBZAOBQPGCF-UHFFFAOYSA-N 4-(1,2-dimethyl-4-naphthalen-2-yl-3,4-dihydro-1H-isoquinolin-7-yl)morpholine Chemical compound CN1C(C2=CC(=CC=C2C(C1)C1=CC2=CC=CC=C2C=C1)N1CCOCC1)C UVOXBZAOBQPGCF-UHFFFAOYSA-N 0.000 claims 1
- SOFZYEOTERJVNQ-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2OC(C3C4=CC=CC=C4CNC3)=CC2=C1 SOFZYEOTERJVNQ-UHFFFAOYSA-N 0.000 claims 1
- YGJFEAYNAPIHFM-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)-2,4-dimethyl-7-pyridazin-3-yl-1,3-dihydroisoquinoline Chemical compound C=1C=C2C(C)(C=3OC4=CC=CC=C4C=3)CN(C)CC2=CC=1C1=CC=CN=N1 YGJFEAYNAPIHFM-UHFFFAOYSA-N 0.000 claims 1
- YDRCMLFPZXPXHO-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)-2,8-dimethyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC(C)=C2CN(C)CC1C1=CC2=CC=CC=C2O1 YDRCMLFPZXPXHO-UHFFFAOYSA-N 0.000 claims 1
- ZQAUOGJHBUZJJC-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)-2-ethyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(CC)CC(C=3OC4=CC=CC=C4C=3)C2=CC=C1C1=CC=CN=N1 ZQAUOGJHBUZJJC-UHFFFAOYSA-N 0.000 claims 1
- RZJIBBZPHONNCB-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)-2-methyl-7-pyridazin-3-yl-1,3-dihydroisoquinolin-4-ol Chemical compound C=1C=C2C(O)(C=3OC4=CC=CC=C4C=3)CN(C)CC2=CC=1C1=CC=CN=N1 RZJIBBZPHONNCB-UHFFFAOYSA-N 0.000 claims 1
- BBPUKASYEVSYPJ-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1H-isoquinolin-8-ol Chemical compound OC1=C2CN(C)CC(C=3OC4=CC=CC=C4C=3)C2=CC=C1C1=CC=CN=N1 BBPUKASYEVSYPJ-UHFFFAOYSA-N 0.000 claims 1
- UBPCUEVRWJIHLS-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3OC4=CC=CC=C4C=3)C2=CC=C1C1=CC=CN=N1 UBPCUEVRWJIHLS-UHFFFAOYSA-N 0.000 claims 1
- CEYRKFCKAOHYOS-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)-5-fluoro-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3OC4=CC=CC=C4C=3)C2=C(F)C=C1C1=CC=CN=N1 CEYRKFCKAOHYOS-UHFFFAOYSA-N 0.000 claims 1
- QYGONWYOOYMNOI-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)-6-fluoro-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3OC4=CC=CC=C4C=3)C2=CC(F)=C1C1=CC=CN=N1 QYGONWYOOYMNOI-UHFFFAOYSA-N 0.000 claims 1
- DXZQVLGABAOCPT-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)-7-(6-methoxypyrazin-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=CN=CC(C=2C=C3CN(C)CC(C3=CC=2)C=2OC3=CC=CC=C3C=2)=N1 DXZQVLGABAOCPT-UHFFFAOYSA-N 0.000 claims 1
- OBAMHIRCFUIFTN-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)-7-fluoro-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=C(F)C=C2CN(C)CC1C1=CC2=CC=CC=C2O1 OBAMHIRCFUIFTN-UHFFFAOYSA-N 0.000 claims 1
- DZULUOWCXNJGTE-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)-8-fluoro-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3OC4=CC=CC=C4C=3)C2=CC=C1C1=CC=CN=N1 DZULUOWCXNJGTE-UHFFFAOYSA-N 0.000 claims 1
- GAORYRDNACCEKO-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)-8-fluoro-2-methyl-7-pyridazin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3OC4=CC=CC=C4C=3)C2=CC=C1C1=CC=NN=C1 GAORYRDNACCEKO-UHFFFAOYSA-N 0.000 claims 1
- VLKXLXHPTXPHST-UHFFFAOYSA-N 4-(1-benzofuran-3-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C4=CC=CC=C4OC=3)C2=CC=C1C1=CC=CN=N1 VLKXLXHPTXPHST-UHFFFAOYSA-N 0.000 claims 1
- LORHLUOWSHIGEA-UHFFFAOYSA-N 4-(1-benzofuran-4-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=4C=COC=4C=CC=3)C2=CC=C1C1=CC=CN=N1 LORHLUOWSHIGEA-UHFFFAOYSA-N 0.000 claims 1
- CWESITNZBWEBQM-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-1-methyl-1,2,3,4-tetrahydroisoquinoline Chemical compound C12=CC=CC=C2C(C)NCC1C1=CC=C(OC=C2)C2=C1 CWESITNZBWEBQM-UHFFFAOYSA-N 0.000 claims 1
- PCVVWFZJRMUQGT-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-2,8-dimethyl-7-pyrazin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound CC1=C2CN(C)CC(C=3C=C4C=COC4=CC=3)C2=CC=C1C1=CN=CC=N1 PCVVWFZJRMUQGT-UHFFFAOYSA-N 0.000 claims 1
- AKAWSTYIHWJLTK-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-2-methyl-1,3-dihydroisoquinoline-4-carbonitrile Chemical compound C1=C2OC=CC2=CC(C2(C#N)C3=CC=CC=C3CN(C2)C)=C1 AKAWSTYIHWJLTK-UHFFFAOYSA-N 0.000 claims 1
- IAJAJSFFAOWOSX-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-ol Chemical compound C12=CC=C(O)C=C2CN(C)CC1C1=CC=C(OC=C2)C2=C1 IAJAJSFFAOWOSX-UHFFFAOYSA-N 0.000 claims 1
- WDRVVIBTXUJNIN-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-2-methyl-3,4-dihydro-1h-isoquinoline-7-carbonitrile Chemical compound C12=CC=C(C#N)C=C2CN(C)CC1C1=CC=C(OC=C2)C2=C1 WDRVVIBTXUJNIN-UHFFFAOYSA-N 0.000 claims 1
- GPXBDLIDGPNLIU-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-2-methyl-7-(6-methylpyridazin-3-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=COC4=CC=3)C2=CC=C1C1=CC=C(C)N=N1 GPXBDLIDGPNLIU-UHFFFAOYSA-N 0.000 claims 1
- ZXXSBBLZUFQOAY-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-2-methyl-7-morpholin-4-yl-1,3-dihydroisoquinolin-4-ol Chemical compound C=1C=C2C(O)(C=3C=C4C=COC4=CC=3)CN(C)CC2=CC=1N1CCOCC1 ZXXSBBLZUFQOAY-UHFFFAOYSA-N 0.000 claims 1
- WODUQJGRKOUEKK-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-2-methyl-7-pyrazin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=COC4=CC=3)C2=CC=C1C1=CN=CC=N1 WODUQJGRKOUEKK-UHFFFAOYSA-N 0.000 claims 1
- UZQYUNYXCRPSIH-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-2-methyl-7-pyridazin-3-yl-1,3-dihydroisoquinolin-4-ol Chemical compound C=1C=C2C(O)(C=3C=C4C=COC4=CC=3)CN(C)CC2=CC=1C1=CC=CN=N1 UZQYUNYXCRPSIH-UHFFFAOYSA-N 0.000 claims 1
- FTWDMVSMXMZGEH-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1H-isoquinolin-8-ol Chemical compound OC1=C2CN(C)CC(C=3C=C4C=COC4=CC=3)C2=CC=C1C1=CC=CN=N1 FTWDMVSMXMZGEH-UHFFFAOYSA-N 0.000 claims 1
- HIDUCBFFNKDJTE-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-2-methyl-7-pyridazin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=COC4=CC=3)C2=CC=C1C1=CC=NN=C1 HIDUCBFFNKDJTE-UHFFFAOYSA-N 0.000 claims 1
- AZDVTGIPZPAVID-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-2-methyl-7-pyrimidin-2-yl-3,4-dihydro-1H-isoquinolin-8-ol Chemical compound OC1=C2CN(C)CC(C=3C=C4C=COC4=CC=3)C2=CC=C1C1=NC=CC=N1 AZDVTGIPZPAVID-UHFFFAOYSA-N 0.000 claims 1
- WKXJSDHPOCEGDU-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-4-fluoro-2-methyl-1,3-dihydroisoquinoline Chemical compound C1=C2OC=CC2=CC(C2(F)C3=CC=CC=C3CN(C2)C)=C1 WKXJSDHPOCEGDU-UHFFFAOYSA-N 0.000 claims 1
- FSSQALTXFWBAIB-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-6-fluoro-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=COC4=CC=3)C2=CC(F)=C1C1=CC=CN=N1 FSSQALTXFWBAIB-UHFFFAOYSA-N 0.000 claims 1
- IPFCEBFEXHCGTJ-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-7-(3-methoxypyrazin-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=NC=CN=C1C1=CC=C(C(CN(C)C2)C=3C=C4C=COC4=CC=3)C2=C1 IPFCEBFEXHCGTJ-UHFFFAOYSA-N 0.000 claims 1
- ALBRZLDWKLGMPN-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-7-(6-methoxypyrazin-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=CN=CC(C=2C=C3CN(C)CC(C3=CC=2)C=2C=C3C=COC3=CC=2)=N1 ALBRZLDWKLGMPN-UHFFFAOYSA-N 0.000 claims 1
- KRTDQGRKCAOJRL-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-7-fluoro-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=C(F)C=C2CN(C)CC1C1=CC=C(OC=C2)C2=C1 KRTDQGRKCAOJRL-UHFFFAOYSA-N 0.000 claims 1
- QLYPCYVJFJJERE-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-7-methoxy-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2OC=CC2=CC(C2C3=CC=C(C=C3CN(C)C2)OC)=C1 QLYPCYVJFJJERE-UHFFFAOYSA-N 0.000 claims 1
- CYMDOFMALPOJHK-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-8-fluoro-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC(F)=C2CN(C)CC1C1=CC=C(OC=C2)C2=C1 CYMDOFMALPOJHK-UHFFFAOYSA-N 0.000 claims 1
- TUXYQUAHLANLNV-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-8-fluoro-2-methyl-7-pyrimidin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3C=C4C=COC4=CC=3)C2=CC=C1C1=NC=CC=N1 TUXYQUAHLANLNV-UHFFFAOYSA-N 0.000 claims 1
- QKZNONHEBKBDLE-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-8-fluoro-2-methyl-7-pyrimidin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3C=C4C=COC4=CC=3)C2=CC=C1C1=CC=NC=N1 QKZNONHEBKBDLE-UHFFFAOYSA-N 0.000 claims 1
- HTMWAOYYFNWYFE-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-8-methoxy-2-methyl-7-pyrimidin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=C2CN(C)CC(C=3C=C4C=COC4=CC=3)C2=CC=C1C1=CC=NC=N1 HTMWAOYYFNWYFE-UHFFFAOYSA-N 0.000 claims 1
- VTEHKHOICGJUSO-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-8-methoxy-2-methyl-7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=C2CN(C)CC(C=3C=C4C=COC4=CC=3)C2=CC=C1C1=CN=CN=C1 VTEHKHOICGJUSO-UHFFFAOYSA-N 0.000 claims 1
- WGLMWYZWOPBOMO-UHFFFAOYSA-N 4-(1-benzofuran-6-yl)-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=C2C=COC2=CC(C2C3=CC=CC=C3CNC2)=C1 WGLMWYZWOPBOMO-UHFFFAOYSA-N 0.000 claims 1
- DTNIZPFSXRZZEQ-UHFFFAOYSA-N 4-(1-benzofuran-6-yl)-2,8-dimethyl-7-pyrimidin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound CC1=C2CN(C)CC(C=3C=C4OC=CC4=CC=3)C2=CC=C1C1=CC=NC=N1 DTNIZPFSXRZZEQ-UHFFFAOYSA-N 0.000 claims 1
- MXSDKQNVDLNGCI-UHFFFAOYSA-N 4-(1-benzofuran-6-yl)-2-methyl-7-(3-methylpyrazin-2-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4OC=CC4=CC=3)C2=CC=C1C1=NC=CN=C1C MXSDKQNVDLNGCI-UHFFFAOYSA-N 0.000 claims 1
- YOXGFACSXWSIEM-UHFFFAOYSA-N 4-(1-benzofuran-6-yl)-2-methyl-7-(6-methylpyrazin-2-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4OC=CC4=CC=3)C2=CC=C1C1=CN=CC(C)=N1 YOXGFACSXWSIEM-UHFFFAOYSA-N 0.000 claims 1
- ZRUYSDKYUZTEID-UHFFFAOYSA-N 4-(1-benzofuran-6-yl)-2-methyl-7-[6-(trifluoromethyl)pyridazin-3-yl]-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4OC=CC4=CC=3)C2=CC=C1C1=CC=C(C(F)(F)F)N=N1 ZRUYSDKYUZTEID-UHFFFAOYSA-N 0.000 claims 1
- UWNFTDGNQWHZPO-UHFFFAOYSA-N 4-(1-benzofuran-6-yl)-2-methyl-7-morpholin-4-yl-3,4-dihydro-1h-isoquinolin-8-ol Chemical compound OC1=C2CN(C)CC(C=3C=C4OC=CC4=CC=3)C2=CC=C1N1CCOCC1 UWNFTDGNQWHZPO-UHFFFAOYSA-N 0.000 claims 1
- PWOUJUJSQMFMMS-UHFFFAOYSA-N 4-(1-benzofuran-6-yl)-2-methyl-7-pyridazin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4OC=CC4=CC=3)C2=CC=C1C1=CC=NN=C1 PWOUJUJSQMFMMS-UHFFFAOYSA-N 0.000 claims 1
- FZGZGOMETUAOIG-UHFFFAOYSA-N 4-(1-benzofuran-6-yl)-2-methyl-7-pyrimidin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4OC=CC4=CC=3)C2=CC=C1C1=NC=CC=N1 FZGZGOMETUAOIG-UHFFFAOYSA-N 0.000 claims 1
- YPZLHKXYONMQRG-UHFFFAOYSA-N 4-(1-benzofuran-6-yl)-2-methyl-7-pyrimidin-4-yl-3,4-dihydro-1H-isoquinolin-8-ol Chemical compound OC1=C2CN(C)CC(C=3C=C4OC=CC4=CC=3)C2=CC=C1C1=CC=NC=N1 YPZLHKXYONMQRG-UHFFFAOYSA-N 0.000 claims 1
- VUGUFLHNLSGSGS-UHFFFAOYSA-N 4-(1-benzofuran-6-yl)-2-methyl-7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4OC=CC4=CC=3)C2=CC=C1C1=CN=CN=C1 VUGUFLHNLSGSGS-UHFFFAOYSA-N 0.000 claims 1
- KNISWSZAMIYKMI-UHFFFAOYSA-N 4-(1-benzofuran-6-yl)-6-fluoro-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4OC=CC4=CC=3)C2=CC(F)=C1C1=CC=CN=N1 KNISWSZAMIYKMI-UHFFFAOYSA-N 0.000 claims 1
- NWYHVVQYIRXTFP-UHFFFAOYSA-N 4-(1-benzofuran-6-yl)-7-(3-methoxypyrazin-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=NC=CN=C1C1=CC=C(C(CN(C)C2)C=3C=C4OC=CC4=CC=3)C2=C1 NWYHVVQYIRXTFP-UHFFFAOYSA-N 0.000 claims 1
- DQRJLUNYBNWREZ-UHFFFAOYSA-N 4-(1-benzofuran-6-yl)-7-(6-methoxypyrazin-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=CN=CC(C=2C=C3CN(C)CC(C3=CC=2)C=2C=C3OC=CC3=CC=2)=N1 DQRJLUNYBNWREZ-UHFFFAOYSA-N 0.000 claims 1
- KBXBVDUWEAIUKG-UHFFFAOYSA-N 4-(1-benzofuran-6-yl)-8-fluoro-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3C=C4OC=CC4=CC=3)C2=CC=C1C1=CC=CN=N1 KBXBVDUWEAIUKG-UHFFFAOYSA-N 0.000 claims 1
- CRIXEMGYWQKRRJ-UHFFFAOYSA-N 4-(1-benzofuran-6-yl)-8-fluoro-2-methyl-7-pyridazin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3C=C4OC=CC4=CC=3)C2=CC=C1C1=CC=NN=C1 CRIXEMGYWQKRRJ-UHFFFAOYSA-N 0.000 claims 1
- CZZMHUTYFYHTBV-UHFFFAOYSA-N 4-(1-benzofuran-6-yl)-8-fluoro-2-methyl-7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3C=C4OC=CC4=CC=3)C2=CC=C1C1=CN=CN=C1 CZZMHUTYFYHTBV-UHFFFAOYSA-N 0.000 claims 1
- PHZUPZIELRXSLL-UHFFFAOYSA-N 4-(1-benzofuran-6-yl)-8-methoxy-2-methyl-7-pyrimidin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=C2CN(C)CC(C=3C=C4OC=CC4=CC=3)C2=CC=C1C1=NC=CC=N1 PHZUPZIELRXSLL-UHFFFAOYSA-N 0.000 claims 1
- SCNQXZMXILXZRI-UHFFFAOYSA-N 4-(1-benzofuran-7-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=CC2=C1OC=C2 SCNQXZMXILXZRI-UHFFFAOYSA-N 0.000 claims 1
- RUARZXMFMVXHST-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2SC(C3C4=CC=CC=C4CNC3)=CC2=C1 RUARZXMFMVXHST-UHFFFAOYSA-N 0.000 claims 1
- MRKTVQPJMKKRBS-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-2,4-dimethyl-7-pyridazin-3-yl-1,3-dihydroisoquinoline Chemical compound C=1C=C2C(C)(C=3SC4=CC=CC=C4C=3)CN(C)CC2=CC=1C1=CC=CN=N1 MRKTVQPJMKKRBS-UHFFFAOYSA-N 0.000 claims 1
- UWFQIWIIMHYHFD-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline-7-carbonitrile Chemical compound C12=CC=C(C#N)C=C2CN(C)CC1C1=CC2=CC=CC=C2S1 UWFQIWIIMHYHFD-UHFFFAOYSA-N 0.000 claims 1
- JGYKKPVTHZOZEG-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-2-methyl-7-(piperidin-1-ylmethyl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1CN1CCCCC1 JGYKKPVTHZOZEG-UHFFFAOYSA-N 0.000 claims 1
- PHKIJCIUAIEWQH-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-2-methyl-7-[6-(trifluoromethyl)pyridazin-3-yl]-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1C1=CC=C(C(F)(F)F)N=N1 PHKIJCIUAIEWQH-UHFFFAOYSA-N 0.000 claims 1
- YNICATWZLIOGMV-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-2-methyl-7-morpholin-4-yl-1,3-dihydroisoquinolin-4-ol Chemical compound C=1C=C2C(O)(C=3SC4=CC=CC=C4C=3)CN(C)CC2=CC=1N1CCOCC1 YNICATWZLIOGMV-UHFFFAOYSA-N 0.000 claims 1
- HAQQTPCJCLWUMT-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-2-methyl-7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1C1=CN=CN=C1 HAQQTPCJCLWUMT-UHFFFAOYSA-N 0.000 claims 1
- KBBFSXINVNDJIE-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-4-methoxy-2-methyl-1,3-dihydroisoquinoline Chemical compound C1=CC=C2SC(C3(C4=CC=CC=C4CN(C)C3)OC)=CC2=C1 KBBFSXINVNDJIE-UHFFFAOYSA-N 0.000 claims 1
- OGBOKWKEQHNZIF-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-7-methoxy-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C1=CC=C2SC(C3C4=CC=C(C=C4CN(C)C3)OC)=CC2=C1 OGBOKWKEQHNZIF-UHFFFAOYSA-N 0.000 claims 1
- RLPCKFFTXOAFOK-UHFFFAOYSA-N 4-(1-benzothiophen-4-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=CC2=C1C=CS2 RLPCKFFTXOAFOK-UHFFFAOYSA-N 0.000 claims 1
- YNNJOPWSTUKHSK-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-1,2-dimethyl-7-piperidin-1-yl-3,4-dihydro-1H-isoquinoline Chemical compound S1C2=C(C=C1)C=C(C=C2)C1CN(C(C2=CC(=CC=C12)N1CCCCC1)C)C YNNJOPWSTUKHSK-UHFFFAOYSA-N 0.000 claims 1
- ZTPDOHWQXSHCBH-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-1,2-dimethyl-7-pyrrolidin-1-yl-3,4-dihydro-1H-isoquinoline Chemical compound S1C2=C(C=C1)C=C(C=C2)C1CN(C(C2=CC(=CC=C12)N1CCCC1)C)C ZTPDOHWQXSHCBH-UHFFFAOYSA-N 0.000 claims 1
- ZTTGGYXKRQGNFT-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-1-methyl-1,2,3,4-tetrahydroisoquinoline Chemical compound C12=CC=CC=C2C(C)NCC1C1=CC=C(SC=C2)C2=C1 ZTTGGYXKRQGNFT-UHFFFAOYSA-N 0.000 claims 1
- OCOUSRUBBMODOC-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2,4-dimethyl-7-pyridazin-3-yl-1,3-dihydroisoquinoline Chemical compound C=1C=C2C(C)(C=3C=C4C=CSC4=CC=3)CN(C)CC2=CC=1C1=CC=CN=N1 OCOUSRUBBMODOC-UHFFFAOYSA-N 0.000 claims 1
- BJXVQFAPZIHUSZ-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2,8-dimethyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC(C)=C2CN(C)CC1C1=CC=C(SC=C2)C2=C1 BJXVQFAPZIHUSZ-UHFFFAOYSA-N 0.000 claims 1
- RSVPRFPYJHTZFN-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2,8-dimethyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound CC1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=CC=CN=N1 RSVPRFPYJHTZFN-UHFFFAOYSA-N 0.000 claims 1
- MSAOCUIZZQRLFM-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2,8-dimethyl-7-pyrimidin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound CC1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=NC=CC=N1 MSAOCUIZZQRLFM-UHFFFAOYSA-N 0.000 claims 1
- WNGUWAMNNKUKTP-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2,8-dimethyl-7-pyrimidin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound CC1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=CC=NC=N1 WNGUWAMNNKUKTP-UHFFFAOYSA-N 0.000 claims 1
- INHJPRRMGVDLEX-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2,8-dimethyl-7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinoline Chemical compound CC1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=CN=CN=C1 INHJPRRMGVDLEX-UHFFFAOYSA-N 0.000 claims 1
- JZYSWJLODKRMRN-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2-ethyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(CC)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=CC=CN=N1 JZYSWJLODKRMRN-UHFFFAOYSA-N 0.000 claims 1
- ZDZGDSLKDOSHHZ-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-ol Chemical compound C12=CC=C(O)C=C2CN(C)CC1C1=CC=C(SC=C2)C2=C1 ZDZGDSLKDOSHHZ-UHFFFAOYSA-N 0.000 claims 1
- MHFUBIDIXOMIAL-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=C(SC=C2)C2=C1 MHFUBIDIXOMIAL-UHFFFAOYSA-N 0.000 claims 1
- GCZHHWMFRCHBTE-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2-methyl-7-(1,2,4-triazin-6-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=CN=CN=N1 GCZHHWMFRCHBTE-UHFFFAOYSA-N 0.000 claims 1
- PCRGAYGTUZDOSO-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2-methyl-7-(4-methylpiperazin-1-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1CN(C)CCN1C1=CC=C(C(CN(C)C2)C=3C=C4C=CSC4=CC=3)C2=C1 PCRGAYGTUZDOSO-UHFFFAOYSA-N 0.000 claims 1
- FOTPZKWBSSAQKF-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2-methyl-7-methylsulfonyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=C(S(C)(=O)=O)C=C2CN(C)CC1C1=CC=C(SC=C2)C2=C1 FOTPZKWBSSAQKF-UHFFFAOYSA-N 0.000 claims 1
- UKJPVMDORVWEHI-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2-methyl-7-morpholin-4-yl-1,3-dihydroisoquinolin-4-ol Chemical compound C=1C=C2C(O)(C=3C=C4C=CSC4=CC=3)CN(C)CC2=CC=1N1CCOCC1 UKJPVMDORVWEHI-UHFFFAOYSA-N 0.000 claims 1
- QUUWQCBFDZIYFX-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2-methyl-7-piperidin-1-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1N1CCCCC1 QUUWQCBFDZIYFX-UHFFFAOYSA-N 0.000 claims 1
- IHVBZAGLVLDTKO-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2-methyl-7-pyrazin-2-yl-3,4-dihydro-1H-isoquinolin-8-ol Chemical compound OC1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=CN=CC=N1 IHVBZAGLVLDTKO-UHFFFAOYSA-N 0.000 claims 1
- RDUPJQANIXJRRN-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2-methyl-7-pyrimidin-2-yl-3,4-dihydro-1H-isoquinolin-8-ol Chemical compound OC1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=NC=CC=N1 RDUPJQANIXJRRN-UHFFFAOYSA-N 0.000 claims 1
- HVORMACWMNLOQL-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-4-fluoro-2-methyl-1,3-dihydroisoquinoline Chemical compound C1=C2SC=CC2=CC(C2(F)C3=CC=CC=C3CN(C2)C)=C1 HVORMACWMNLOQL-UHFFFAOYSA-N 0.000 claims 1
- MGDYJLKTEJHQTH-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-7-(6-methoxypyrazin-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=CN=CC(C=2C=C3CN(C)CC(C3=CC=2)C=2C=C3C=CSC3=CC=2)=N1 MGDYJLKTEJHQTH-UHFFFAOYSA-N 0.000 claims 1
- BWQWQATWHINLBZ-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-7-fluoro-2-methyl-1,3-dihydroisoquinolin-4-ol Chemical compound C1=C2SC=CC2=CC(C2(O)C3=CC=C(F)C=C3CN(C2)C)=C1 BWQWQATWHINLBZ-UHFFFAOYSA-N 0.000 claims 1
- KFMSZRUIBIGOHD-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-8-fluoro-2-methyl-3,4-dihydro-1h-isoquinoline-7-carbonitrile Chemical compound C12=CC=C(C#N)C(F)=C2CN(C)CC1C1=CC=C(SC=C2)C2=C1 KFMSZRUIBIGOHD-UHFFFAOYSA-N 0.000 claims 1
- NKLOAWWGCIPFQU-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-8-methoxy-2-methyl-7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=CN=CN=C1 NKLOAWWGCIPFQU-UHFFFAOYSA-N 0.000 claims 1
- CBQJEXYJIGVKCJ-UHFFFAOYSA-N 4-(1-benzothiophen-6-yl)-1,2-dimethyl-7-pyrrolidin-1-yl-3,4-dihydro-1H-isoquinoline Chemical compound S1C2=C(C=C1)C=CC(=C2)C1CN(C(C2=CC(=CC=C12)N1CCCC1)C)C CBQJEXYJIGVKCJ-UHFFFAOYSA-N 0.000 claims 1
- VUOJJAIZEDLHAX-UHFFFAOYSA-N 4-(1-benzothiophen-6-yl)-1-methyl-1,2,3,4-tetrahydroisoquinoline Chemical compound C12=CC=CC=C2C(C)NCC1C1=CC=C(C=CS2)C2=C1 VUOJJAIZEDLHAX-UHFFFAOYSA-N 0.000 claims 1
- MBLKRTKMFCIZHR-UHFFFAOYSA-N 4-(1-benzothiophen-6-yl)-2,8-dimethyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC(C)=C2CN(C)CC1C1=CC=C(C=CS2)C2=C1 MBLKRTKMFCIZHR-UHFFFAOYSA-N 0.000 claims 1
- IUYDJUYJGKBLDW-UHFFFAOYSA-N 4-(1-benzothiophen-6-yl)-2,8-dimethyl-7-pyrimidin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound CC1=C2CN(C)CC(C=3C=C4SC=CC4=CC=3)C2=CC=C1C1=CC=NC=N1 IUYDJUYJGKBLDW-UHFFFAOYSA-N 0.000 claims 1
- JNEMMEXYDDQCHU-UHFFFAOYSA-N 4-(1-benzothiophen-6-yl)-2,8-dimethyl-7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinoline Chemical compound CC1=C2CN(C)CC(C=3C=C4SC=CC4=CC=3)C2=CC=C1C1=CN=CN=C1 JNEMMEXYDDQCHU-UHFFFAOYSA-N 0.000 claims 1
- IXGVNGRODMOXAQ-UHFFFAOYSA-N 4-(1-benzothiophen-6-yl)-2-ethyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(CC)CC(C=3C=C4SC=CC4=CC=3)C2=CC=C1C1=CC=CN=N1 IXGVNGRODMOXAQ-UHFFFAOYSA-N 0.000 claims 1
- ATPOFQNQTNJMEQ-UHFFFAOYSA-N 4-(1-benzothiophen-6-yl)-2-methyl-7-(4-methylpiperazin-1-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1CN(C)CCN1C1=CC=C(C(CN(C)C2)C=3C=C4SC=CC4=CC=3)C2=C1 ATPOFQNQTNJMEQ-UHFFFAOYSA-N 0.000 claims 1
- SFXBOPLUQGVOHI-UHFFFAOYSA-N 4-(1-benzothiophen-6-yl)-2-methyl-7-morpholin-4-yl-1,3-dihydroisoquinolin-4-ol Chemical compound C=1C=C2C(O)(C=3C=C4SC=CC4=CC=3)CN(C)CC2=CC=1N1CCOCC1 SFXBOPLUQGVOHI-UHFFFAOYSA-N 0.000 claims 1
- CQWXYTVPDUMSAX-UHFFFAOYSA-N 4-(1-benzothiophen-6-yl)-2-methyl-7-morpholin-4-yl-3,4-dihydro-1h-isoquinolin-8-ol Chemical compound OC1=C2CN(C)CC(C=3C=C4SC=CC4=CC=3)C2=CC=C1N1CCOCC1 CQWXYTVPDUMSAX-UHFFFAOYSA-N 0.000 claims 1
- QTAGOFPCVAMXOK-UHFFFAOYSA-N 4-(1-benzothiophen-6-yl)-2-methyl-7-pyrazin-2-yl-3,4-dihydro-1H-isoquinolin-8-ol Chemical compound OC1=C2CN(C)CC(C=3C=C4SC=CC4=CC=3)C2=CC=C1C1=CN=CC=N1 QTAGOFPCVAMXOK-UHFFFAOYSA-N 0.000 claims 1
- PYOMFNGFGWKFSP-UHFFFAOYSA-N 4-(1-benzothiophen-6-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4SC=CC4=CC=3)C2=CC=C1C1=CC=CN=N1 PYOMFNGFGWKFSP-UHFFFAOYSA-N 0.000 claims 1
- BNVKDBJKVCNJOK-UHFFFAOYSA-N 4-(1-benzothiophen-6-yl)-2-methyl-7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinolin-8-ol Chemical compound OC1=C2CN(C)CC(C=3C=C4SC=CC4=CC=3)C2=CC=C1C1=CN=CN=C1 BNVKDBJKVCNJOK-UHFFFAOYSA-N 0.000 claims 1
- YCWJRHFUESJJDB-UHFFFAOYSA-N 4-(1-benzothiophen-6-yl)-4-fluoro-2-methyl-1,3-dihydroisoquinoline Chemical compound C1=C2C=CSC2=CC(C2(F)C3=CC=CC=C3CN(C2)C)=C1 YCWJRHFUESJJDB-UHFFFAOYSA-N 0.000 claims 1
- IIQRXBZPDUYHBY-UHFFFAOYSA-N 4-(1-benzothiophen-6-yl)-8-fluoro-2-methyl-7-pyridazin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3C=C4SC=CC4=CC=3)C2=CC=C1C1=CC=NN=C1 IIQRXBZPDUYHBY-UHFFFAOYSA-N 0.000 claims 1
- WGUXCSDSFSUPGS-UHFFFAOYSA-N 4-(1-benzothiophen-6-yl)-8-fluoro-2-methyl-7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3C=C4SC=CC4=CC=3)C2=CC=C1C1=CN=CN=C1 WGUXCSDSFSUPGS-UHFFFAOYSA-N 0.000 claims 1
- CFUHORQJAJFNTA-UHFFFAOYSA-N 4-(1-benzothiophen-7-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=CC2=C1SC=C2 CFUHORQJAJFNTA-UHFFFAOYSA-N 0.000 claims 1
- RSGSDRBLKCGILO-UHFFFAOYSA-N 4-(1-benzothiophen-7-yl)-8-fluoro-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC(F)=C2CN(C)CC1C1=CC=CC2=C1SC=C2 RSGSDRBLKCGILO-UHFFFAOYSA-N 0.000 claims 1
- NLZIRPYWNAJSPN-UHFFFAOYSA-N 4-(1-fluoronaphthalen-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C(=C4C=CC=CC4=CC=3)F)C2=CC=C1C1=CC=CN=N1 NLZIRPYWNAJSPN-UHFFFAOYSA-N 0.000 claims 1
- UEZALJJDPFGZJS-UHFFFAOYSA-N 4-(1-methoxynaphthalen-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=CC2=CC=CC=C2C(OC)=C1C(C1=CC=2)CN(C)CC1=CC=2C1=CC=CN=N1 UEZALJJDPFGZJS-UHFFFAOYSA-N 0.000 claims 1
- HZNUQFGGAOYIOF-UHFFFAOYSA-N 4-(1H-indol-2-yl)-1,2-dimethyl-7-piperidin-1-yl-3,4-dihydro-1H-isoquinoline Chemical compound N1C(=CC2=CC=CC=C12)C1CN(C(C2=CC(=CC=C12)N1CCCCC1)C)C HZNUQFGGAOYIOF-UHFFFAOYSA-N 0.000 claims 1
- BDRRBFQSQQPUBY-UHFFFAOYSA-N 4-(1H-indol-6-yl)-1,2-dimethyl-7-pyrrolidin-1-yl-3,4-dihydro-1H-isoquinoline Chemical compound N1C=CC2=CC=C(C=C12)C1CN(C(C2=CC(=CC=C12)N1CCCC1)C)C BDRRBFQSQQPUBY-UHFFFAOYSA-N 0.000 claims 1
- ANWMRVPYLBMPQM-UHFFFAOYSA-N 4-(1h-indazol-4-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=CC2=C1C=NN2 ANWMRVPYLBMPQM-UHFFFAOYSA-N 0.000 claims 1
- QSCKJSANWQIPQT-UHFFFAOYSA-N 4-(1h-indazol-5-yl)-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=C2NN=CC2=CC(C2C3=CC=CC=C3CNC2)=C1 QSCKJSANWQIPQT-UHFFFAOYSA-N 0.000 claims 1
- VGLQANACODNYOM-UHFFFAOYSA-N 4-(1h-indazol-5-yl)-1,2-dimethyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2C(C)N(C)CC1C1=CC=C(NN=C2)C2=C1 VGLQANACODNYOM-UHFFFAOYSA-N 0.000 claims 1
- UTQXSMOPSLMDRX-UHFFFAOYSA-N 4-(1h-indazol-5-yl)-2,4-dimethyl-1,3-dihydroisoquinoline Chemical compound C1=C2NN=CC2=CC(C2(C)C3=CC=CC=C3CN(C2)C)=C1 UTQXSMOPSLMDRX-UHFFFAOYSA-N 0.000 claims 1
- GMTLJASVUGLEEV-UHFFFAOYSA-N 4-(1h-indazol-5-yl)-2,7-dimethyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=C(C)C=C2CN(C)CC1C1=CC=C(NN=C2)C2=C1 GMTLJASVUGLEEV-UHFFFAOYSA-N 0.000 claims 1
- JRUNWUCFSINWFW-UHFFFAOYSA-N 4-(1h-indazol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=C(NN=C2)C2=C1 JRUNWUCFSINWFW-UHFFFAOYSA-N 0.000 claims 1
- VCULOLZHWWIHIN-UHFFFAOYSA-N 4-(1h-indazol-5-yl)-2-methyl-7-[6-(trifluoromethyl)pyridazin-3-yl]-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=NNC4=CC=3)C2=CC=C1C1=CC=C(C(F)(F)F)N=N1 VCULOLZHWWIHIN-UHFFFAOYSA-N 0.000 claims 1
- PTPPWVCPSSKJSZ-UHFFFAOYSA-N 4-(1h-indazol-5-yl)-2-methyl-7-piperidin-1-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=NNC4=CC=3)C2=CC=C1N1CCCCC1 PTPPWVCPSSKJSZ-UHFFFAOYSA-N 0.000 claims 1
- XGLKYCFOLYYCGT-UHFFFAOYSA-N 4-(1h-indazol-5-yl)-2-methyl-7-pyrazin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=NNC4=CC=3)C2=CC=C1C1=CN=CC=N1 XGLKYCFOLYYCGT-UHFFFAOYSA-N 0.000 claims 1
- DBNYGAGVBWNPBJ-UHFFFAOYSA-N 4-(1h-indazol-5-yl)-2-methyl-7-pyridazin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=NNC4=CC=3)C2=CC=C1C1=CC=NN=C1 DBNYGAGVBWNPBJ-UHFFFAOYSA-N 0.000 claims 1
- XVHMEMLEPIVSLS-UHFFFAOYSA-N 4-(1h-indazol-5-yl)-2-methyl-7-pyrimidin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=NNC4=CC=3)C2=CC=C1C1=NC=CC=N1 XVHMEMLEPIVSLS-UHFFFAOYSA-N 0.000 claims 1
- QTGDDQMSXFLYKD-UHFFFAOYSA-N 4-(1h-indazol-5-yl)-2-methyl-7-pyrimidin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=NNC4=CC=3)C2=CC=C1C1=CC=NC=N1 QTGDDQMSXFLYKD-UHFFFAOYSA-N 0.000 claims 1
- JDVSIIJBISEKLQ-UHFFFAOYSA-N 4-(1h-indazol-5-yl)-2-methyl-7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=NNC4=CC=3)C2=CC=C1C1=CN=CN=C1 JDVSIIJBISEKLQ-UHFFFAOYSA-N 0.000 claims 1
- QTWKHCIFFJHSPI-UHFFFAOYSA-N 4-(1h-indazol-6-yl)-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=C2C=NNC2=CC(C2C3=CC=CC=C3CNC2)=C1 QTWKHCIFFJHSPI-UHFFFAOYSA-N 0.000 claims 1
- SXGWUHXJZYXYKO-UHFFFAOYSA-N 4-(1h-indazol-6-yl)-2,4-dimethyl-1,3-dihydroisoquinoline Chemical compound C1=C2C=NNC2=CC(C2(C)C3=CC=CC=C3CN(C2)C)=C1 SXGWUHXJZYXYKO-UHFFFAOYSA-N 0.000 claims 1
- PIJRDIFVKLZSQX-UHFFFAOYSA-N 4-(1h-indazol-6-yl)-2,7-dimethyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=C(C)C=C2CN(C)CC1C1=CC=C(C=NN2)C2=C1 PIJRDIFVKLZSQX-UHFFFAOYSA-N 0.000 claims 1
- KQGQSHMUDYGYQE-UHFFFAOYSA-N 4-(1h-indazol-6-yl)-2,8-dimethyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC(C)=C2CN(C)CC1C1=CC=C(C=NN2)C2=C1 KQGQSHMUDYGYQE-UHFFFAOYSA-N 0.000 claims 1
- YIULBCYXFWYXAX-UHFFFAOYSA-N 4-(1h-indazol-6-yl)-2-methyl-7-[6-(trifluoromethyl)pyridazin-3-yl]-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4NN=CC4=CC=3)C2=CC=C1C1=CC=C(C(F)(F)F)N=N1 YIULBCYXFWYXAX-UHFFFAOYSA-N 0.000 claims 1
- TVNCOPUQOKBKLG-UHFFFAOYSA-N 4-(1h-indazol-6-yl)-2-methyl-7-pyrazin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4NN=CC4=CC=3)C2=CC=C1C1=CN=CC=N1 TVNCOPUQOKBKLG-UHFFFAOYSA-N 0.000 claims 1
- YGTCFGFJEJAYMO-UHFFFAOYSA-N 4-(1h-indol-2-yl)-1,2-dimethyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2C(C)N(C)CC1C1=CC2=CC=CC=C2N1 YGTCFGFJEJAYMO-UHFFFAOYSA-N 0.000 claims 1
- KPGKPBZCACDYIF-UHFFFAOYSA-N 4-(1h-indol-2-yl)-2,7-dimethyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=C(C)C=C2CN(C)CC1C1=CC2=CC=CC=C2N1 KPGKPBZCACDYIF-UHFFFAOYSA-N 0.000 claims 1
- RTTFZVZVLDNMQU-UHFFFAOYSA-N 4-(1h-indol-2-yl)-2,8-dimethyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC(C)=C2CN(C)CC1C1=CC2=CC=CC=C2N1 RTTFZVZVLDNMQU-UHFFFAOYSA-N 0.000 claims 1
- JHUZVOYTGZJVOY-UHFFFAOYSA-N 4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-ol Chemical compound C12=CC=C(O)C=C2CN(C)CC1C1=CC2=CC=CC=C2N1 JHUZVOYTGZJVOY-UHFFFAOYSA-N 0.000 claims 1
- OHDWMVBDJNEJKN-UHFFFAOYSA-N 4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline-7-carbonitrile Chemical compound C12=CC=C(C#N)C=C2CN(C)CC1C1=CC2=CC=CC=C2N1 OHDWMVBDJNEJKN-UHFFFAOYSA-N 0.000 claims 1
- RBTICQVEMDORLY-UHFFFAOYSA-N 4-(1h-indol-2-yl)-2-methyl-7-(3-methylpyrazin-2-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1C1=NC=CN=C1C RBTICQVEMDORLY-UHFFFAOYSA-N 0.000 claims 1
- JFRUNWRBAXATEZ-UHFFFAOYSA-N 4-(1h-indol-2-yl)-2-methyl-7-(6-methylpyrazin-2-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1C1=CN=CC(C)=N1 JFRUNWRBAXATEZ-UHFFFAOYSA-N 0.000 claims 1
- NYBLCGFVGOZWKA-UHFFFAOYSA-N 4-(1h-indol-2-yl)-2-methyl-7-morpholin-4-yl-3,4-dihydro-1h-isoquinolin-8-ol Chemical compound OC1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1N1CCOCC1 NYBLCGFVGOZWKA-UHFFFAOYSA-N 0.000 claims 1
- GEUPABHSEKEJJC-UHFFFAOYSA-N 4-(1h-indol-2-yl)-2-methyl-7-piperidin-1-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1N1CCCCC1 GEUPABHSEKEJJC-UHFFFAOYSA-N 0.000 claims 1
- LVPRNHARJCVNQO-UHFFFAOYSA-N 4-(1h-indol-2-yl)-2-methyl-7-pyrazin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1C1=CN=CC=N1 LVPRNHARJCVNQO-UHFFFAOYSA-N 0.000 claims 1
- HYLFMTVLJKBKBO-UHFFFAOYSA-N 4-(1h-indol-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1C1=CC=CN=N1 HYLFMTVLJKBKBO-UHFFFAOYSA-N 0.000 claims 1
- KBMMWQIBAVKXKP-UHFFFAOYSA-N 4-(1h-indol-2-yl)-2-methyl-7-pyridazin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1C1=CC=NN=C1 KBMMWQIBAVKXKP-UHFFFAOYSA-N 0.000 claims 1
- JGGKZJJJHATABW-UHFFFAOYSA-N 4-(1h-indol-2-yl)-2-methyl-7-pyrimidin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1C1=NC=CC=N1 JGGKZJJJHATABW-UHFFFAOYSA-N 0.000 claims 1
- YBLSYHHYDJGJQM-UHFFFAOYSA-N 4-(1h-indol-2-yl)-2-methyl-7-pyrimidin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1C1=CC=NC=N1 YBLSYHHYDJGJQM-UHFFFAOYSA-N 0.000 claims 1
- PJDDFZMZVDVGGJ-UHFFFAOYSA-N 4-(1h-indol-2-yl)-2-methyl-7-pyrrolidin-1-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1N1CCCC1 PJDDFZMZVDVGGJ-UHFFFAOYSA-N 0.000 claims 1
- MDCMBPWVWHUQJZ-UHFFFAOYSA-N 4-(1h-indol-2-yl)-7-(6-methoxypyrazin-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=CN=CC(C=2C=C3CN(C)CC(C3=CC=2)C=2NC3=CC=CC=C3C=2)=N1 MDCMBPWVWHUQJZ-UHFFFAOYSA-N 0.000 claims 1
- UDGKJLIEUPSNTB-UHFFFAOYSA-N 4-(1h-indol-5-yl)-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=C2NC=CC2=CC(C2C3=CC=CC=C3CNC2)=C1 UDGKJLIEUPSNTB-UHFFFAOYSA-N 0.000 claims 1
- XKKRGLOOJLOADN-UHFFFAOYSA-N 4-(1h-indol-5-yl)-1,2-dimethyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2C(C)N(C)CC1C1=CC=C(NC=C2)C2=C1 XKKRGLOOJLOADN-UHFFFAOYSA-N 0.000 claims 1
- QTLFHBRRGGBXPO-UHFFFAOYSA-N 4-(1h-indol-5-yl)-2,8-dimethyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC(C)=C2CN(C)CC1C1=CC=C(NC=C2)C2=C1 QTLFHBRRGGBXPO-UHFFFAOYSA-N 0.000 claims 1
- ULJQDMZVAWULNT-UHFFFAOYSA-N 4-(1h-indol-5-yl)-2-methyl-1,3-dihydroisoquinolin-4-ol Chemical compound C1=C2NC=CC2=CC(C2(O)C3=CC=CC=C3CN(C2)C)=C1 ULJQDMZVAWULNT-UHFFFAOYSA-N 0.000 claims 1
- JWDOVGMELWAWSX-UHFFFAOYSA-N 4-(1h-indol-5-yl)-2-methyl-1,3-dihydroisoquinoline-4-carbonitrile Chemical compound C1=C2NC=CC2=CC(C2(C#N)C3=CC=CC=C3CN(C2)C)=C1 JWDOVGMELWAWSX-UHFFFAOYSA-N 0.000 claims 1
- AMOJYVUHZUQQBZ-UHFFFAOYSA-N 4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-ol Chemical compound C12=CC=C(O)C=C2CN(C)CC1C1=CC=C(NC=C2)C2=C1 AMOJYVUHZUQQBZ-UHFFFAOYSA-N 0.000 claims 1
- AAHLCKVWZXFMPB-UHFFFAOYSA-N 4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=C(NC=C2)C2=C1 AAHLCKVWZXFMPB-UHFFFAOYSA-N 0.000 claims 1
- MBAARLCAYZZKIH-UHFFFAOYSA-N 4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinoline-7-carbonitrile Chemical compound C12=CC=C(C#N)C=C2CN(C)CC1C1=CC=C(NC=C2)C2=C1 MBAARLCAYZZKIH-UHFFFAOYSA-N 0.000 claims 1
- LIJGDKXLCOMTEF-UHFFFAOYSA-N 4-(1h-indol-5-yl)-2-methyl-7-(3-methylpyrazin-2-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CNC4=CC=3)C2=CC=C1C1=NC=CN=C1C LIJGDKXLCOMTEF-UHFFFAOYSA-N 0.000 claims 1
- CJGUAOVTAZMTRF-UHFFFAOYSA-N 4-(1h-indol-5-yl)-2-methyl-7-(6-methylpyrazin-2-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CNC4=CC=3)C2=CC=C1C1=CN=CC(C)=N1 CJGUAOVTAZMTRF-UHFFFAOYSA-N 0.000 claims 1
- JGJRCERQOURLMH-UHFFFAOYSA-N 4-(1h-indol-5-yl)-2-methyl-7-(6-methylpyridazin-3-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CNC4=CC=3)C2=CC=C1C1=CC=C(C)N=N1 JGJRCERQOURLMH-UHFFFAOYSA-N 0.000 claims 1
- JTYOEVOPLCFKFG-UHFFFAOYSA-N 4-(1h-indol-5-yl)-2-methyl-7-morpholin-4-yl-1,3-dihydroisoquinolin-4-ol Chemical compound C=1C=C2C(O)(C=3C=C4C=CNC4=CC=3)CN(C)CC2=CC=1N1CCOCC1 JTYOEVOPLCFKFG-UHFFFAOYSA-N 0.000 claims 1
- OBXITEVKXRTRNN-UHFFFAOYSA-N 4-(1h-indol-5-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CNC4=CC=3)C2=CC=C1C1=CC=CN=N1 OBXITEVKXRTRNN-UHFFFAOYSA-N 0.000 claims 1
- CADQBKWAXNWCIM-UHFFFAOYSA-N 4-(1h-indol-5-yl)-2-methyl-7-pyridazin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CNC4=CC=3)C2=CC=C1C1=CC=NN=C1 CADQBKWAXNWCIM-UHFFFAOYSA-N 0.000 claims 1
- JDYGMBHVNWSUGT-UHFFFAOYSA-N 4-(1h-indol-5-yl)-2-methyl-7-pyrimidin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CNC4=CC=3)C2=CC=C1C1=CC=NC=N1 JDYGMBHVNWSUGT-UHFFFAOYSA-N 0.000 claims 1
- XKEFXQLFHRECHN-UHFFFAOYSA-N 4-(1h-indol-5-yl)-2-methyl-7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CNC4=CC=3)C2=CC=C1C1=CN=CN=C1 XKEFXQLFHRECHN-UHFFFAOYSA-N 0.000 claims 1
- GBRGDTOGGXRSHA-UHFFFAOYSA-N 4-(1h-indol-5-yl)-2-methyl-7-pyrrolidin-1-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CNC4=CC=3)C2=CC=C1N1CCCC1 GBRGDTOGGXRSHA-UHFFFAOYSA-N 0.000 claims 1
- BVLLRQFXDLNCRZ-UHFFFAOYSA-N 4-(1h-indol-5-yl)-7-(3-methoxypyrazin-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=NC=CN=C1C1=CC=C(C(CN(C)C2)C=3C=C4C=CNC4=CC=3)C2=C1 BVLLRQFXDLNCRZ-UHFFFAOYSA-N 0.000 claims 1
- OBZUTWFAQMDOIH-UHFFFAOYSA-N 4-(1h-indol-6-yl)-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=C2C=CNC2=CC(C2C3=CC=CC=C3CNC2)=C1 OBZUTWFAQMDOIH-UHFFFAOYSA-N 0.000 claims 1
- VDSDPYVHJLBFBG-UHFFFAOYSA-N 4-(1h-indol-6-yl)-2,4-dimethyl-1,3-dihydroisoquinoline Chemical compound C1=C2C=CNC2=CC(C2(C)C3=CC=CC=C3CN(C2)C)=C1 VDSDPYVHJLBFBG-UHFFFAOYSA-N 0.000 claims 1
- ABKXGSOOUIXHKU-UHFFFAOYSA-N 4-(1h-indol-6-yl)-2,7-dimethyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=C(C)C=C2CN(C)CC1C1=CC=C(C=CN2)C2=C1 ABKXGSOOUIXHKU-UHFFFAOYSA-N 0.000 claims 1
- IXLULEIDIYROLR-UHFFFAOYSA-N 4-(1h-indol-6-yl)-2-methyl-1,3-dihydroisoquinoline-4-carbonitrile Chemical compound C1=C2C=CNC2=CC(C2(C#N)C3=CC=CC=C3CN(C2)C)=C1 IXLULEIDIYROLR-UHFFFAOYSA-N 0.000 claims 1
- XVOHCFDLTKSDBT-UHFFFAOYSA-N 4-(1h-indol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-ol Chemical compound C12=CC=C(O)C=C2CN(C)CC1C1=CC=C(C=CN2)C2=C1 XVOHCFDLTKSDBT-UHFFFAOYSA-N 0.000 claims 1
- OKVFRSLHLRTWEP-UHFFFAOYSA-N 4-(1h-indol-6-yl)-2-methyl-7-(3-methylpyrazin-2-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4NC=CC4=CC=3)C2=CC=C1C1=NC=CN=C1C OKVFRSLHLRTWEP-UHFFFAOYSA-N 0.000 claims 1
- UUBHOUWOKIMUIT-UHFFFAOYSA-N 4-(1h-indol-6-yl)-2-methyl-7-(6-methylpyrazin-2-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4NC=CC4=CC=3)C2=CC=C1C1=CN=CC(C)=N1 UUBHOUWOKIMUIT-UHFFFAOYSA-N 0.000 claims 1
- DAZQYPVYKVPLNG-UHFFFAOYSA-N 4-(1h-indol-6-yl)-2-methyl-7-(6-methylpyridazin-3-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4NC=CC4=CC=3)C2=CC=C1C1=CC=C(C)N=N1 DAZQYPVYKVPLNG-UHFFFAOYSA-N 0.000 claims 1
- NVVVUBWMMORPOG-UHFFFAOYSA-N 4-(1h-indol-6-yl)-2-methyl-7-[6-(trifluoromethyl)pyridazin-3-yl]-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4NC=CC4=CC=3)C2=CC=C1C1=CC=C(C(F)(F)F)N=N1 NVVVUBWMMORPOG-UHFFFAOYSA-N 0.000 claims 1
- PVYYJVQUTSZPRT-UHFFFAOYSA-N 4-(1h-indol-6-yl)-2-methyl-7-piperidin-1-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4NC=CC4=CC=3)C2=CC=C1N1CCCCC1 PVYYJVQUTSZPRT-UHFFFAOYSA-N 0.000 claims 1
- LYSSCJHNEOLJFB-UHFFFAOYSA-N 4-(1h-indol-6-yl)-2-methyl-7-pyrazin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4NC=CC4=CC=3)C2=CC=C1C1=CN=CC=N1 LYSSCJHNEOLJFB-UHFFFAOYSA-N 0.000 claims 1
- VHIZHVCTTQLNRC-UHFFFAOYSA-N 4-(1h-indol-6-yl)-2-methyl-7-pyrimidin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4NC=CC4=CC=3)C2=CC=C1C1=CC=NC=N1 VHIZHVCTTQLNRC-UHFFFAOYSA-N 0.000 claims 1
- VKEHZCCKBZAFNY-UHFFFAOYSA-N 4-(1h-indol-6-yl)-2-methyl-7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4NC=CC4=CC=3)C2=CC=C1C1=CN=CN=C1 VKEHZCCKBZAFNY-UHFFFAOYSA-N 0.000 claims 1
- VXIHNYDTJDCBTK-UHFFFAOYSA-N 4-(1h-indol-6-yl)-2-methyl-7-pyrrolidin-1-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4NC=CC4=CC=3)C2=CC=C1N1CCCC1 VXIHNYDTJDCBTK-UHFFFAOYSA-N 0.000 claims 1
- JMJYDTIRGHLCHH-UHFFFAOYSA-N 4-(1h-indol-6-yl)-7-(6-methoxypyrazin-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=CN=CC(C=2C=C3CN(C)CC(C3=CC=2)C=2C=C3NC=CC3=CC=2)=N1 JMJYDTIRGHLCHH-UHFFFAOYSA-N 0.000 claims 1
- ASXZYNMHCLSAOI-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-5-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=C(OCC2)C2=C1 ASXZYNMHCLSAOI-UHFFFAOYSA-N 0.000 claims 1
- YWXLYUCTGCJFLD-UHFFFAOYSA-N 4-(2,4-dimethyl-4-naphthalen-2-yl-1,3-dihydroisoquinolin-7-yl)morpholine Chemical compound C=1C=C2C(C)(C=3C=C4C=CC=CC4=CC=3)CN(C)CC2=CC=1N1CCOCC1 YWXLYUCTGCJFLD-UHFFFAOYSA-N 0.000 claims 1
- XBLKWTZVUAGRIC-UHFFFAOYSA-N 4-(2,8-dimethyl-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinolin-7-yl)morpholine Chemical compound CC1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1N1CCOCC1 XBLKWTZVUAGRIC-UHFFFAOYSA-N 0.000 claims 1
- MGQXHZNYVJYIEL-UHFFFAOYSA-N 4-(2-chloro-1-benzothiophen-5-yl)-2-methyl-7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=C(Cl)SC4=CC=3)C2=CC=C1C1=CN=CN=C1 MGQXHZNYVJYIEL-UHFFFAOYSA-N 0.000 claims 1
- FIKIRFTYPGMKAQ-UHFFFAOYSA-N 4-(2-chloro-1-benzothiophen-6-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4SC(Cl)=CC4=CC=3)C2=CC=C1C1=CC=CN=N1 FIKIRFTYPGMKAQ-UHFFFAOYSA-N 0.000 claims 1
- RSSVEVIMRIAKNG-UHFFFAOYSA-N 4-(2-ethyl-8-fluoro-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinolin-7-yl)morpholine Chemical compound FC1=C2CN(CC)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1N1CCOCC1 RSSVEVIMRIAKNG-UHFFFAOYSA-N 0.000 claims 1
- LKEZWDNAQQISJT-UHFFFAOYSA-N 4-(2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)-1,2-benzothiazole Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=CC2=C1C=NS2 LKEZWDNAQQISJT-UHFFFAOYSA-N 0.000 claims 1
- NUCLMJIPFUTECQ-UHFFFAOYSA-N 4-(2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)-1,2-benzoxazole Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=CC2=C1C=NO2 NUCLMJIPFUTECQ-UHFFFAOYSA-N 0.000 claims 1
- CYOGIJCYIWQBCA-UHFFFAOYSA-N 4-(2-methyl-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinolin-7-yl)morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1N1CCOCC1 CYOGIJCYIWQBCA-UHFFFAOYSA-N 0.000 claims 1
- MNEWFTUHRRQSEA-UHFFFAOYSA-N 4-(2-methyl-4-phthalazin-6-yl-3,4-dihydro-1h-isoquinolin-7-yl)morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=NN=CC4=CC=3)C2=CC=C1N1CCOCC1 MNEWFTUHRRQSEA-UHFFFAOYSA-N 0.000 claims 1
- LQFRZTWPAUGOLT-UHFFFAOYSA-N 4-(2-methyl-4-pyrazolo[1,5-a]pyridin-6-yl-3,4-dihydro-1h-isoquinolin-7-yl)morpholine Chemical compound C1=C2CN(C)CC(C3=CN4N=CC=C4C=C3)C2=CC=C1N1CCOCC1 LQFRZTWPAUGOLT-UHFFFAOYSA-N 0.000 claims 1
- HYEVIMQFFRWTRW-UHFFFAOYSA-N 4-(2-methyl-4-quinazolin-7-yl-3,4-dihydro-1h-isoquinolin-7-yl)morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4N=CN=CC4=CC=3)C2=CC=C1N1CCOCC1 HYEVIMQFFRWTRW-UHFFFAOYSA-N 0.000 claims 1
- CGZFUSINSVZKIT-UHFFFAOYSA-N 4-(2-methyl-4-thieno[2,3-b]pyridin-5-yl-3,4-dihydro-1h-isoquinolin-7-yl)morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CSC4=NC=3)C2=CC=C1N1CCOCC1 CGZFUSINSVZKIT-UHFFFAOYSA-N 0.000 claims 1
- NASNNRSDCJQYJP-UHFFFAOYSA-N 4-(3-chloronaphthalen-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C(=CC4=CC=CC=C4C=3)Cl)C2=CC=C1C1=CC=CN=N1 NASNNRSDCJQYJP-UHFFFAOYSA-N 0.000 claims 1
- ZWIATSQWXGEOLI-UHFFFAOYSA-N 4-(3-methoxynaphthalen-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=CC2=CC=CC=C2C=C1C(C1=CC=2)CN(C)CC1=CC=2C1=CC=CN=N1 ZWIATSQWXGEOLI-UHFFFAOYSA-N 0.000 claims 1
- OVZPQIIDWJTPTR-UHFFFAOYSA-N 4-(4-chloronaphthalen-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=CC4=C(Cl)C=3)C2=CC=C1C1=CC=CN=N1 OVZPQIIDWJTPTR-UHFFFAOYSA-N 0.000 claims 1
- LNWDITHPTDSRHR-UHFFFAOYSA-N 4-(4-fluoronaphthalen-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=CC4=C(F)C=3)C2=CC=C1C1=CC=CN=N1 LNWDITHPTDSRHR-UHFFFAOYSA-N 0.000 claims 1
- OFGGCHRXBAFWKI-UHFFFAOYSA-N 4-(4-imidazo[1,2-a]pyridin-7-yl-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)morpholine Chemical compound C1=C2CN(C)CC(C3=CC4=NC=CN4C=C3)C2=CC=C1N1CCOCC1 OFGGCHRXBAFWKI-UHFFFAOYSA-N 0.000 claims 1
- YXYHOKFEGZGQNF-UHFFFAOYSA-N 4-(5-chloro-1-benzofuran-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC2=CC(Cl)=CC=C2O1 YXYHOKFEGZGQNF-UHFFFAOYSA-N 0.000 claims 1
- SIYJSQFNNGCTET-UHFFFAOYSA-N 4-(5-chloronaphthalen-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=C(Cl)C4=CC=3)C2=CC=C1C1=CC=CN=N1 SIYJSQFNNGCTET-UHFFFAOYSA-N 0.000 claims 1
- DHVHDBDATNUDKK-UHFFFAOYSA-N 4-(5-fluoro-1-benzofuran-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3OC4=CC=C(F)C=C4C=3)C2=CC=C1C1=CC=CN=N1 DHVHDBDATNUDKK-UHFFFAOYSA-N 0.000 claims 1
- BMXGYGWMUXBWBO-UHFFFAOYSA-N 4-(5-fluoro-1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC2=CC(F)=CC=C2S1 BMXGYGWMUXBWBO-UHFFFAOYSA-N 0.000 claims 1
- CSSIJQPSTRHHAD-UHFFFAOYSA-N 4-(5-fluoro-2-methyl-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinolin-7-yl)morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=C(F)C=C1N1CCOCC1 CSSIJQPSTRHHAD-UHFFFAOYSA-N 0.000 claims 1
- IZGKAOIJKJUKCN-UHFFFAOYSA-N 4-(5-methoxy-1-benzofuran-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C1N(C)CC2=CC=CC=C2C1C1=CC2=CC(OC)=CC=C2O1 IZGKAOIJKJUKCN-UHFFFAOYSA-N 0.000 claims 1
- RTWSXLOMFKHXCK-UHFFFAOYSA-N 4-(6-fluoro-1-benzofuran-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3OC4=CC(F)=CC=C4C=3)C2=CC=C1C1=CC=CN=N1 RTWSXLOMFKHXCK-UHFFFAOYSA-N 0.000 claims 1
- CSOVTPURXXVODX-UHFFFAOYSA-N 4-(6-fluoro-1-benzothiophen-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3SC4=CC(F)=CC=C4C=3)C2=CC=C1C1=CC=CN=N1 CSOVTPURXXVODX-UHFFFAOYSA-N 0.000 claims 1
- NCINMKKEVKTKMG-UHFFFAOYSA-N 4-(6-fluoro-2-methyl-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinolin-7-yl)morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC(F)=C1N1CCOCC1 NCINMKKEVKTKMG-UHFFFAOYSA-N 0.000 claims 1
- WMGHGYBOJQZNSH-UHFFFAOYSA-N 4-(6-fluoronaphthalen-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC(F)=CC4=CC=3)C2=CC=C1C1=CC=CN=N1 WMGHGYBOJQZNSH-UHFFFAOYSA-N 0.000 claims 1
- HCROUQBQVDEBCD-UHFFFAOYSA-N 4-(6-methoxynaphthalen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C1N(C)CC2=CC=CC=C2C1C1=CC2=CC=C(OC)C=C2C=C1 HCROUQBQVDEBCD-UHFFFAOYSA-N 0.000 claims 1
- QXZNTYKTHNWRJP-UHFFFAOYSA-N 4-(7-chloronaphthalen-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=C(Cl)C=CC4=CC=3)C2=CC=C1C1=CC=CN=N1 QXZNTYKTHNWRJP-UHFFFAOYSA-N 0.000 claims 1
- WGXNRUNVEHBSEU-UHFFFAOYSA-N 4-(7-fluoro-1-benzofuran-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC2=CC=CC(F)=C2O1 WGXNRUNVEHBSEU-UHFFFAOYSA-N 0.000 claims 1
- BKDZFGJHADTLJY-UHFFFAOYSA-N 4-(7-fluoro-1-benzofuran-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3OC4=C(F)C=CC=C4C=3)C2=CC=C1C1=CC=CN=N1 BKDZFGJHADTLJY-UHFFFAOYSA-N 0.000 claims 1
- GSDQJUUATQGNSC-UHFFFAOYSA-N 4-(7-fluoro-1h-indazol-5-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=NNC4=C(F)C=3)C2=CC=C1C1=CC=CN=N1 GSDQJUUATQGNSC-UHFFFAOYSA-N 0.000 claims 1
- PNJBMSAGOYMZAF-UHFFFAOYSA-N 4-(7-fluoro-1h-indazol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2C=NNC2=C(F)C(C2CN(CC3=CC=CC=C32)C)=C1 PNJBMSAGOYMZAF-UHFFFAOYSA-N 0.000 claims 1
- ODRPKURYZBIFAU-UHFFFAOYSA-N 4-(7-fluoro-1h-indol-6-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C(=C4NC=CC4=CC=3)F)C2=CC=C1C1=CC=CN=N1 ODRPKURYZBIFAU-UHFFFAOYSA-N 0.000 claims 1
- RFXMRGWMRFXABT-UHFFFAOYSA-N 4-(7-fluoronaphthalen-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=C(F)C=CC4=CC=3)C2=CC=C1C1=CC=CN=N1 RFXMRGWMRFXABT-UHFFFAOYSA-N 0.000 claims 1
- OXERSMRQMIRNOS-UHFFFAOYSA-N 4-(7-methoxy-1-benzofuran-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C1N(C)CC2=CC=CC=C2C1C1=CC(C=CC=C2OC)=C2O1 OXERSMRQMIRNOS-UHFFFAOYSA-N 0.000 claims 1
- VVIFYPNCGJKEGE-UHFFFAOYSA-N 4-(7-methoxy-1-benzothiophen-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-ol Chemical compound C1N(C)CC2=CC(O)=CC=C2C1C1=C(OC)C(SC=C2)=C2C=C1 VVIFYPNCGJKEGE-UHFFFAOYSA-N 0.000 claims 1
- RMTRWPALOKPQFS-UHFFFAOYSA-N 4-(7-methoxy-1-benzothiophen-6-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C1N(C)CC2=CC=CC=C2C1C1=C(OC)C(SC=C2)=C2C=C1 RMTRWPALOKPQFS-UHFFFAOYSA-N 0.000 claims 1
- YEMBUOUHISOBHC-UHFFFAOYSA-N 4-(7-methoxy-1h-indazol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C1N(C)CC2=CC=CC=C2C1C(C=C1OC)=CC2=C1NN=C2 YEMBUOUHISOBHC-UHFFFAOYSA-N 0.000 claims 1
- UZQLKTBMZGBMFL-UHFFFAOYSA-N 4-(7-methoxynaphthalen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C1N(C)CC2=CC=CC=C2C1C1=CC2=CC(OC)=CC=C2C=C1 UZQLKTBMZGBMFL-UHFFFAOYSA-N 0.000 claims 1
- MVKMRRFLTMLQTM-UHFFFAOYSA-N 4-(7-methoxynaphthalen-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C=1C2=CC(OC)=CC=C2C=CC=1C(C1=CC=2)CN(C)CC1=CC=2C1=CC=CN=N1 MVKMRRFLTMLQTM-UHFFFAOYSA-N 0.000 claims 1
- SORPVEHSIQFALS-UHFFFAOYSA-N 4-(8-chloronaphthalen-2-yl)-2-methyl-1,3-dihydroisoquinolin-4-ol Chemical compound C1=CC=C(Cl)C2=CC(C3(O)C4=CC=CC=C4CN(C3)C)=CC=C21 SORPVEHSIQFALS-UHFFFAOYSA-N 0.000 claims 1
- JAGAWHYDIAQPDU-UHFFFAOYSA-N 4-(8-chloronaphthalen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-ol Chemical compound C12=CC=C(O)C=C2CN(C)CC1C1=CC=C(C=CC=C2Cl)C2=C1 JAGAWHYDIAQPDU-UHFFFAOYSA-N 0.000 claims 1
- IVPCGLTVOQTZRX-UHFFFAOYSA-N 4-(8-chloronaphthalen-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C(Cl)=CC=CC4=CC=3)C2=CC=C1C1=CC=CN=N1 IVPCGLTVOQTZRX-UHFFFAOYSA-N 0.000 claims 1
- HVLQTTWMMUWBKN-UHFFFAOYSA-N 4-(8-fluoro-2-methyl-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinolin-7-yl)morpholine Chemical compound FC1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1N1CCOCC1 HVLQTTWMMUWBKN-UHFFFAOYSA-N 0.000 claims 1
- HJFVNUAHRGIUEN-UHFFFAOYSA-N 4-(8-fluoronaphthalen-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C(F)=CC=CC4=CC=3)C2=CC=C1C1=CC=CN=N1 HJFVNUAHRGIUEN-UHFFFAOYSA-N 0.000 claims 1
- JGIFZPUMTQDWJD-UHFFFAOYSA-N 4-(8-methoxynaphthalen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-ol Chemical compound C1N(C)CC2=CC(O)=CC=C2C1C1=CC=C2C=CC=C(OC)C2=C1 JGIFZPUMTQDWJD-UHFFFAOYSA-N 0.000 claims 1
- JAKVAVFNBYQZOD-UHFFFAOYSA-N 4-(8-methoxynaphthalen-2-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2C(OC)=CC=CC2=CC=C1C(C1=CC=2)CN(C)CC1=CC=2C1=CC=CN=N1 JAKVAVFNBYQZOD-UHFFFAOYSA-N 0.000 claims 1
- UQSGIMVBXPUHAB-UHFFFAOYSA-N 4-[1-[4-(1-benzofuran-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]cyclopropyl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4OC=CC4=CC=3)C2=CC=C1C1(N2CCOCC2)CC1 UQSGIMVBXPUHAB-UHFFFAOYSA-N 0.000 claims 1
- XGWVMMQCGOPTOB-UHFFFAOYSA-N 4-[1-[4-(1-benzothiophen-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]cyclopropyl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4SC=CC4=CC=3)C2=CC=C1C1(N2CCOCC2)CC1 XGWVMMQCGOPTOB-UHFFFAOYSA-N 0.000 claims 1
- IDPDEJASJAPNFD-UHFFFAOYSA-N 4-[1-[4-(1h-indazol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]cyclopropyl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=NNC4=CC=3)C2=CC=C1C1(N2CCOCC2)CC1 IDPDEJASJAPNFD-UHFFFAOYSA-N 0.000 claims 1
- SWGIAJOBIDYIFA-UHFFFAOYSA-N 4-[1-[4-(1h-indazol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]cyclopropyl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4NN=CC4=CC=3)C2=CC=C1C1(N2CCOCC2)CC1 SWGIAJOBIDYIFA-UHFFFAOYSA-N 0.000 claims 1
- KAUPSJIFBLCPQE-UHFFFAOYSA-N 4-[1-[4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]cyclopropyl]morpholine Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1C1(N2CCOCC2)CC1 KAUPSJIFBLCPQE-UHFFFAOYSA-N 0.000 claims 1
- NYVGZZHEOFCAQF-UHFFFAOYSA-N 4-[1-[4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]cyclopropyl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CNC4=CC=3)C2=CC=C1C1(N2CCOCC2)CC1 NYVGZZHEOFCAQF-UHFFFAOYSA-N 0.000 claims 1
- VJVYIOVTWSMBTR-UHFFFAOYSA-N 4-[1-[4-(1h-indol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]cyclopropyl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4NC=CC4=CC=3)C2=CC=C1C1(N2CCOCC2)CC1 VJVYIOVTWSMBTR-UHFFFAOYSA-N 0.000 claims 1
- AAYRVGUNVAAPHQ-UHFFFAOYSA-N 4-[2-[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]propan-2-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1C(C)(C)N1CCOCC1 AAYRVGUNVAAPHQ-UHFFFAOYSA-N 0.000 claims 1
- VBTJYMUVKOJOEE-UHFFFAOYSA-N 4-[2-[4-(1-benzothiophen-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]propan-2-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4SC=CC4=CC=3)C2=CC=C1C(C)(C)N1CCOCC1 VBTJYMUVKOJOEE-UHFFFAOYSA-N 0.000 claims 1
- UDFJGTZSZLPFGO-UHFFFAOYSA-N 4-[2-[4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]propan-2-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1C(C)(C)N1CCOCC1 UDFJGTZSZLPFGO-UHFFFAOYSA-N 0.000 claims 1
- XTGJSBRPGWORPB-UHFFFAOYSA-N 4-[2-[4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]propan-2-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CNC4=CC=3)C2=CC=C1C(C)(C)N1CCOCC1 XTGJSBRPGWORPB-UHFFFAOYSA-N 0.000 claims 1
- AZXIVUXGFCCCCV-UHFFFAOYSA-N 4-[2-[4-(1h-indol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]propan-2-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4NC=CC4=CC=3)C2=CC=C1C(C)(C)N1CCOCC1 AZXIVUXGFCCCCV-UHFFFAOYSA-N 0.000 claims 1
- ZOXIEGAFQCKDGR-UHFFFAOYSA-N 4-[2-ethyl-4-(1h-indol-2-yl)-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(CC)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1N1CCOCC1 ZOXIEGAFQCKDGR-UHFFFAOYSA-N 0.000 claims 1
- CFKIYERKBKLYES-UHFFFAOYSA-N 4-[2-methyl-4-(1-methylindol-2-yl)-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3N(C4=CC=CC=C4C=3)C)C2=CC=C1N1CCOCC1 CFKIYERKBKLYES-UHFFFAOYSA-N 0.000 claims 1
- STDYPIZXLKHNRG-UHFFFAOYSA-N 4-[2-methyl-4-(1-methylindol-5-yl)-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CN(C)C4=CC=3)C2=CC=C1N1CCOCC1 STDYPIZXLKHNRG-UHFFFAOYSA-N 0.000 claims 1
- QNBQABCPRXLYPA-UHFFFAOYSA-N 4-[2-methyl-4-(1-methylnaphthalen-2-yl)-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C(=C4C=CC=CC4=CC=3)C)C2=CC=C1N1CCOCC1 QNBQABCPRXLYPA-UHFFFAOYSA-N 0.000 claims 1
- SDCLPFYPNHIIMK-UHFFFAOYSA-N 4-[2-methyl-4-(5-methylnaphthalen-2-yl)-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=C(C)C4=CC=3)C2=CC=C1N1CCOCC1 SDCLPFYPNHIIMK-UHFFFAOYSA-N 0.000 claims 1
- RZRJXFUESIEUKS-UHFFFAOYSA-N 4-[2-methyl-4-(6-methylsulfonylnaphthalen-2-yl)-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC(=CC4=CC=3)S(C)(=O)=O)C2=CC=C1N1CCOCC1 RZRJXFUESIEUKS-UHFFFAOYSA-N 0.000 claims 1
- JQWHLGFPXWAZNZ-UHFFFAOYSA-N 4-[2-methyl-4-([1,2,4]triazolo[4,3-a]pyridin-6-yl)-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C3=CN4C=NN=C4C=C3)C2=CC=C1N1CCOCC1 JQWHLGFPXWAZNZ-UHFFFAOYSA-N 0.000 claims 1
- DLJRYDJFRJNETD-UHFFFAOYSA-N 4-[2-methyl-4-([1,2,4]triazolo[4,3-a]pyridin-7-yl)-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C3=CC4=NN=CN4C=C3)C2=CC=C1N1CCOCC1 DLJRYDJFRJNETD-UHFFFAOYSA-N 0.000 claims 1
- RNFNVCWDDIHPKC-UHFFFAOYSA-N 4-[4-(1,2-benzothiazol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]morpholine Chemical compound CN1CC(C=2C=C3C=NSC3=CC=2)C2=CC=CC=C2C1N1CCOCC1 RNFNVCWDDIHPKC-UHFFFAOYSA-N 0.000 claims 1
- WUKPYMUQGQNTHJ-UHFFFAOYSA-N 4-[4-(1,2-benzothiazol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]morpholine Chemical compound CN1CC(C=2C=C3SN=CC3=CC=2)C2=CC=CC=C2C1N1CCOCC1 WUKPYMUQGQNTHJ-UHFFFAOYSA-N 0.000 claims 1
- HWRCYBVSQPXBTE-UHFFFAOYSA-N 4-[4-(1,3-benzothiazol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]morpholine Chemical compound CN1CC(C=2C=C3N=CSC3=CC=2)C2=CC=CC=C2C1N1CCOCC1 HWRCYBVSQPXBTE-UHFFFAOYSA-N 0.000 claims 1
- MSTLVBRJNQUUAI-UHFFFAOYSA-N 4-[4-(1,3-benzothiazol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]morpholine Chemical compound CN1CC(C=2C=C3SC=NC3=CC=2)C2=CC=CC=C2C1N1CCOCC1 MSTLVBRJNQUUAI-UHFFFAOYSA-N 0.000 claims 1
- ORWWURDFGRRJEZ-UHFFFAOYSA-N 4-[4-(1-benzofuran-2-yl)-1,2-dimethyl-3,4-dihydro-1H-isoquinolin-7-yl]morpholine Chemical compound O1C(=CC2=C1C=CC=C2)C1CN(C(C2=CC(=CC=C12)N1CCOCC1)C)C ORWWURDFGRRJEZ-UHFFFAOYSA-N 0.000 claims 1
- IYZJYFURQNQIQB-UHFFFAOYSA-N 4-[4-(1-benzofuran-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-2,6-dimethylmorpholine Chemical compound C1C(C)OC(C)CN1C1=CC=C(C(CN(C)C2)C=3OC4=CC=CC=C4C=3)C2=C1 IYZJYFURQNQIQB-UHFFFAOYSA-N 0.000 claims 1
- KMIRJJZXWHDUCI-UHFFFAOYSA-N 4-[4-(1-benzofuran-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-3,5-dimethyl-1,2-oxazole Chemical compound C1=C2CN(C)CC(C=3OC4=CC=CC=C4C=3)C2=CC=C1C=1C(C)=NOC=1C KMIRJJZXWHDUCI-UHFFFAOYSA-N 0.000 claims 1
- TZWDAOXEFHXISX-UHFFFAOYSA-N 4-[4-(1-benzofuran-2-yl)-8-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound COC1=C2CN(C)CC(C=3OC4=CC=CC=C4C=3)C2=CC=C1N1CCOCC1 TZWDAOXEFHXISX-UHFFFAOYSA-N 0.000 claims 1
- ZZZDLENGZKGNGK-UHFFFAOYSA-N 4-[4-(1-benzofuran-3-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C4=CC=CC=C4OC=3)C2=CC=C1N1CCOCC1 ZZZDLENGZKGNGK-UHFFFAOYSA-N 0.000 claims 1
- RJJZKQIKFLSWKY-UHFFFAOYSA-N 4-[4-(1-benzofuran-4-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=4C=COC=4C=CC=3)C2=CC=C1N1CCOCC1 RJJZKQIKFLSWKY-UHFFFAOYSA-N 0.000 claims 1
- NOOOVCBBBATSIY-UHFFFAOYSA-N 4-[4-(1-benzofuran-5-yl)-1,2-dimethyl-3,4-dihydro-1H-isoquinolin-7-yl]morpholine Chemical compound O1C=CC2=C1C=CC(=C2)C1CN(C(C2=CC(=CC=C12)N1CCOCC1)C)C NOOOVCBBBATSIY-UHFFFAOYSA-N 0.000 claims 1
- GMRQKCRMUYRRCI-UHFFFAOYSA-N 4-[4-(1-benzofuran-5-yl)-2-ethyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(CC)CC(C=3C=C4C=COC4=CC=3)C2=CC=C1N1CCOCC1 GMRQKCRMUYRRCI-UHFFFAOYSA-N 0.000 claims 1
- GIYWLAIWMFWFEI-UHFFFAOYSA-N 4-[4-(1-benzofuran-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-2,6-dimethylmorpholine Chemical compound C1C(C)OC(C)CN1C1=CC=C(C(CN(C)C2)C=3C=C4C=COC4=CC=3)C2=C1 GIYWLAIWMFWFEI-UHFFFAOYSA-N 0.000 claims 1
- ISXURRBRTHQQQW-UHFFFAOYSA-N 4-[4-(1-benzofuran-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-3,5-dimethyl-1,2-oxazole Chemical compound C1=C2CN(C)CC(C=3C=C4C=COC4=CC=3)C2=CC=C1C=1C(C)=NOC=1C ISXURRBRTHQQQW-UHFFFAOYSA-N 0.000 claims 1
- ZYWJTJYLXSWPFH-UHFFFAOYSA-N 4-[4-(1-benzofuran-5-yl)-5-fluoro-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=COC4=CC=3)C2=C(F)C=C1N1CCOCC1 ZYWJTJYLXSWPFH-UHFFFAOYSA-N 0.000 claims 1
- LVHKTRLKLAQOBI-UHFFFAOYSA-N 4-[4-(1-benzofuran-5-yl)-8-fluoro-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound FC1=C2CN(C)CC(C=3C=C4C=COC4=CC=3)C2=CC=C1N1CCOCC1 LVHKTRLKLAQOBI-UHFFFAOYSA-N 0.000 claims 1
- MWYJMHNVOGHKOI-UHFFFAOYSA-N 4-[4-(1-benzofuran-5-yl)-8-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound COC1=C2CN(C)CC(C=3C=C4C=COC4=CC=3)C2=CC=C1N1CCOCC1 MWYJMHNVOGHKOI-UHFFFAOYSA-N 0.000 claims 1
- REGGINYFBYUQGO-UHFFFAOYSA-N 4-[4-(1-benzofuran-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-3,5-dimethyl-1,2-oxazole Chemical compound C1=C2CN(C)CC(C=3C=C4OC=CC4=CC=3)C2=CC=C1C=1C(C)=NOC=1C REGGINYFBYUQGO-UHFFFAOYSA-N 0.000 claims 1
- QBXFWODTPPXBRX-UHFFFAOYSA-N 4-[4-(1-benzofuran-6-yl)-6-fluoro-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4OC=CC4=CC=3)C2=CC(F)=C1N1CCOCC1 QBXFWODTPPXBRX-UHFFFAOYSA-N 0.000 claims 1
- VIPNFOBDQHJETR-UHFFFAOYSA-N 4-[4-(1-benzothiophen-2-yl)-2,4-dimethyl-1,3-dihydroisoquinolin-7-yl]morpholine Chemical compound C=1C=C2C(C)(C=3SC4=CC=CC=C4C=3)CN(C)CC2=CC=1N1CCOCC1 VIPNFOBDQHJETR-UHFFFAOYSA-N 0.000 claims 1
- AMNYCLHVMIRZDE-UHFFFAOYSA-N 4-[4-(1-benzothiophen-2-yl)-2,8-dimethyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound CC1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1N1CCOCC1 AMNYCLHVMIRZDE-UHFFFAOYSA-N 0.000 claims 1
- WUADTNYTBZAWRJ-UHFFFAOYSA-N 4-[4-(1-benzothiophen-5-yl)-2-ethyl-8-fluoro-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound FC1=C2CN(CC)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1N1CCOCC1 WUADTNYTBZAWRJ-UHFFFAOYSA-N 0.000 claims 1
- QLQQUDCJVQOCBW-UHFFFAOYSA-N 4-[4-(1-benzothiophen-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1N1CCOCC1 QLQQUDCJVQOCBW-UHFFFAOYSA-N 0.000 claims 1
- MIXXYECUPVNHTR-UHFFFAOYSA-N 4-[4-(1-benzothiophen-5-yl)-5-fluoro-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=C(F)C=C1N1CCOCC1 MIXXYECUPVNHTR-UHFFFAOYSA-N 0.000 claims 1
- XKMGPRZTOPMSKJ-UHFFFAOYSA-N 4-[4-(1-benzothiophen-5-yl)-8-fluoro-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound FC1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1N1CCOCC1 XKMGPRZTOPMSKJ-UHFFFAOYSA-N 0.000 claims 1
- VIEPRBOKZLQNKX-UHFFFAOYSA-N 4-[4-(1-benzothiophen-5-yl)-8-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound COC1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1N1CCOCC1 VIEPRBOKZLQNKX-UHFFFAOYSA-N 0.000 claims 1
- CQYXGWPUMHWJHP-UHFFFAOYSA-N 4-[4-(1-benzothiophen-6-yl)-2,4-dimethyl-1,3-dihydroisoquinolin-7-yl]morpholine Chemical compound C=1C=C2C(C)(C=3C=C4SC=CC4=CC=3)CN(C)CC2=CC=1N1CCOCC1 CQYXGWPUMHWJHP-UHFFFAOYSA-N 0.000 claims 1
- QCMVACRHLBOHMB-UHFFFAOYSA-N 4-[4-(1-benzothiophen-6-yl)-2-ethyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(CC)CC(C=3C=C4SC=CC4=CC=3)C2=CC=C1N1CCOCC1 QCMVACRHLBOHMB-UHFFFAOYSA-N 0.000 claims 1
- RAPYOTFVDQSFNZ-UHFFFAOYSA-N 4-[4-(1-benzothiophen-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4SC=CC4=CC=3)C2=CC=C1N1CCOCC1 RAPYOTFVDQSFNZ-UHFFFAOYSA-N 0.000 claims 1
- FHHVHFLLBGEXKF-UHFFFAOYSA-N 4-[4-(1-benzothiophen-6-yl)-5-fluoro-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4SC=CC4=CC=3)C2=C(F)C=C1N1CCOCC1 FHHVHFLLBGEXKF-UHFFFAOYSA-N 0.000 claims 1
- ADAIBMJZGFYQBI-UHFFFAOYSA-N 4-[4-(1-benzothiophen-6-yl)-8-fluoro-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound FC1=C2CN(C)CC(C=3C=C4SC=CC4=CC=3)C2=CC=C1N1CCOCC1 ADAIBMJZGFYQBI-UHFFFAOYSA-N 0.000 claims 1
- IJHOVVHAWCIENO-UHFFFAOYSA-N 4-[4-(1-benzothiophen-7-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=4SC=CC=4C=CC=3)C2=CC=C1N1CCOCC1 IJHOVVHAWCIENO-UHFFFAOYSA-N 0.000 claims 1
- CENMSTBVNWEGDX-UHFFFAOYSA-N 4-[4-(1-chloronaphthalen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C(=C4C=CC=CC4=CC=3)Cl)C2=CC=C1N1CCOCC1 CENMSTBVNWEGDX-UHFFFAOYSA-N 0.000 claims 1
- KKCRAXOXSNMYAV-UHFFFAOYSA-N 4-[4-(1-fluoronaphthalen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C(=C4C=CC=CC4=CC=3)F)C2=CC=C1N1CCOCC1 KKCRAXOXSNMYAV-UHFFFAOYSA-N 0.000 claims 1
- UDLKLSUKGYPVLA-UHFFFAOYSA-N 4-[4-(1H-indol-2-yl)-1,2-dimethyl-3,4-dihydro-1H-isoquinolin-7-yl]morpholine Chemical compound N1C(=CC2=CC=CC=C12)C1CN(C(C2=CC(=CC=C12)N1CCOCC1)C)C UDLKLSUKGYPVLA-UHFFFAOYSA-N 0.000 claims 1
- BZPWUCFNTOSTNT-UHFFFAOYSA-N 4-[4-(1H-indol-5-yl)-1,2-dimethyl-3,4-dihydro-1H-isoquinolin-7-yl]morpholine Chemical compound N1C=CC2=CC(=CC=C12)C1CN(C(C2=CC(=CC=C12)N1CCOCC1)C)C BZPWUCFNTOSTNT-UHFFFAOYSA-N 0.000 claims 1
- FNQIIUCSMYIARY-UHFFFAOYSA-N 4-[4-(1H-indol-6-yl)-1,2-dimethyl-3,4-dihydro-1H-isoquinolin-7-yl]morpholine Chemical compound N1C=CC2=CC=C(C=C12)C1CN(C(C2=CC(=CC=C12)N1CCOCC1)C)C FNQIIUCSMYIARY-UHFFFAOYSA-N 0.000 claims 1
- GGUNTQMIWPCKNS-UHFFFAOYSA-N 4-[4-(1h-indazol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-3,5-dimethyl-1,2-oxazole Chemical compound C1=C2CN(C)CC(C=3C=C4C=NNC4=CC=3)C2=CC=C1C=1C(C)=NOC=1C GGUNTQMIWPCKNS-UHFFFAOYSA-N 0.000 claims 1
- ZXSYLLYUVFOIPW-UHFFFAOYSA-N 4-[4-(1h-indazol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-2,6-dimethylmorpholine Chemical compound C1C(C)OC(C)CN1C1=CC=C(C(CN(C)C2)C=3C=C4NN=CC4=CC=3)C2=C1 ZXSYLLYUVFOIPW-UHFFFAOYSA-N 0.000 claims 1
- CHOUPVVVODAVGX-UHFFFAOYSA-N 4-[4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-2,6-dimethylmorpholine Chemical compound C1C(C)OC(C)CN1C1=CC=C(C(CN(C)C2)C=3NC4=CC=CC=C4C=3)C2=C1 CHOUPVVVODAVGX-UHFFFAOYSA-N 0.000 claims 1
- BOSFQZNDWSGHMJ-UHFFFAOYSA-N 4-[4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-3,5-dimethyl-1,2-oxazole Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1C=1C(C)=NOC=1C BOSFQZNDWSGHMJ-UHFFFAOYSA-N 0.000 claims 1
- DWHWWFHQLIRIGU-UHFFFAOYSA-N 4-[4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1N1CCOCC1 DWHWWFHQLIRIGU-UHFFFAOYSA-N 0.000 claims 1
- XUGXGDUBGJGMMV-UHFFFAOYSA-N 4-[4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-3,5-dimethyl-1,2-oxazole Chemical compound C1=C2CN(C)CC(C=3C=C4C=CNC4=CC=3)C2=CC=C1C=1C(C)=NOC=1C XUGXGDUBGJGMMV-UHFFFAOYSA-N 0.000 claims 1
- TWPOMTORHHOCPD-UHFFFAOYSA-N 4-[4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CNC4=CC=3)C2=CC=C1N1CCOCC1 TWPOMTORHHOCPD-UHFFFAOYSA-N 0.000 claims 1
- PQABYQJTEZBVKI-UHFFFAOYSA-N 4-[4-(1h-indol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-2,6-dimethylmorpholine Chemical compound C1C(C)OC(C)CN1C1=CC=C(C(CN(C)C2)C=3C=C4NC=CC4=CC=3)C2=C1 PQABYQJTEZBVKI-UHFFFAOYSA-N 0.000 claims 1
- GQRHQPUJLIFMNP-UHFFFAOYSA-N 4-[4-(1h-indol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-3,5-dimethyl-1,2-oxazole Chemical compound C1=C2CN(C)CC(C=3C=C4NC=CC4=CC=3)C2=CC=C1C=1C(C)=NOC=1C GQRHQPUJLIFMNP-UHFFFAOYSA-N 0.000 claims 1
- VPFIIZQDMAXSOV-UHFFFAOYSA-N 4-[4-(1h-indol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4NC=CC4=CC=3)C2=CC=C1N1CCOCC1 VPFIIZQDMAXSOV-UHFFFAOYSA-N 0.000 claims 1
- FWFKOSMRZUHRNG-UHFFFAOYSA-N 4-[4-(1h-indol-6-yl)-8-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound COC1=C2CN(C)CC(C=3C=C4NC=CC4=CC=3)C2=CC=C1N1CCOCC1 FWFKOSMRZUHRNG-UHFFFAOYSA-N 0.000 claims 1
- FYPSQGCAHQVTFH-UHFFFAOYSA-N 4-[4-(3-fluoronaphthalen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C(=CC4=CC=CC=C4C=3)F)C2=CC=C1N1CCOCC1 FYPSQGCAHQVTFH-UHFFFAOYSA-N 0.000 claims 1
- ALBSTAYTUCGUQB-UHFFFAOYSA-N 4-[4-(4-chloronaphthalen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=CC4=C(Cl)C=3)C2=CC=C1N1CCOCC1 ALBSTAYTUCGUQB-UHFFFAOYSA-N 0.000 claims 1
- QSSHZCCLNFVUAV-UHFFFAOYSA-N 4-[4-(4-fluoro-1-benzofuran-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3OC4=CC=CC(F)=C4C=3)C2=CC=C1N1CCOCC1 QSSHZCCLNFVUAV-UHFFFAOYSA-N 0.000 claims 1
- IYHSUIASLNPBTB-UHFFFAOYSA-N 4-[4-(4-fluoronaphthalen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=CC4=C(F)C=3)C2=CC=C1N1CCOCC1 IYHSUIASLNPBTB-UHFFFAOYSA-N 0.000 claims 1
- MKLSKJWVXOPIBH-UHFFFAOYSA-N 4-[4-(5-chloronaphthalen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=C(Cl)C4=CC=3)C2=CC=C1N1CCOCC1 MKLSKJWVXOPIBH-UHFFFAOYSA-N 0.000 claims 1
- HHJHDAHSWQXBPD-UHFFFAOYSA-N 4-[4-(5-fluoronaphthalen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=C(F)C4=CC=3)C2=CC=C1N1CCOCC1 HHJHDAHSWQXBPD-UHFFFAOYSA-N 0.000 claims 1
- CPQJDQAYGKEXRE-UHFFFAOYSA-N 4-[4-(6-chloronaphthalen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC(Cl)=CC4=CC=3)C2=CC=C1N1CCOCC1 CPQJDQAYGKEXRE-UHFFFAOYSA-N 0.000 claims 1
- UAZPYCDNJRSAFI-UHFFFAOYSA-N 4-[4-(6-fluoronaphthalen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC(F)=CC4=CC=3)C2=CC=C1N1CCOCC1 UAZPYCDNJRSAFI-UHFFFAOYSA-N 0.000 claims 1
- ACJTXMNMXFFDBZ-UHFFFAOYSA-N 4-[4-(6-methoxynaphthalen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C(C1=CC=2)CN(C)CC1=CC=2N1CCOCC1 ACJTXMNMXFFDBZ-UHFFFAOYSA-N 0.000 claims 1
- FSORZIPVNXVLJG-UHFFFAOYSA-N 4-[4-(7-chloronaphthalen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=C(Cl)C=CC4=CC=3)C2=CC=C1N1CCOCC1 FSORZIPVNXVLJG-UHFFFAOYSA-N 0.000 claims 1
- BMVACVHAHPIJSX-UHFFFAOYSA-N 4-[4-(7-fluoronaphthalen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=C(F)C=CC4=CC=3)C2=CC=C1N1CCOCC1 BMVACVHAHPIJSX-UHFFFAOYSA-N 0.000 claims 1
- BTWYASDAMVHOAV-UHFFFAOYSA-N 4-[4-(7-methoxy-1-benzofuran-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound O1C=2C(OC)=CC=CC=2C=C1C(C1=CC=2)CN(C)CC1=CC=2N1CCOCC1 BTWYASDAMVHOAV-UHFFFAOYSA-N 0.000 claims 1
- AKQNAJPHQHCIKQ-UHFFFAOYSA-N 4-[4-(7-methoxynaphthalen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C=1C2=CC(OC)=CC=C2C=CC=1C(C1=CC=2)CN(C)CC1=CC=2N1CCOCC1 AKQNAJPHQHCIKQ-UHFFFAOYSA-N 0.000 claims 1
- VNOFEKGPGDWDKT-UHFFFAOYSA-N 4-[4-(8-chloronaphthalen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C(Cl)=CC=CC4=CC=3)C2=CC=C1N1CCOCC1 VNOFEKGPGDWDKT-UHFFFAOYSA-N 0.000 claims 1
- FUQFHQFGJJOZAS-UHFFFAOYSA-N 4-[4-(8-fluoronaphthalen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C(F)=CC=CC4=CC=3)C2=CC=C1N1CCOCC1 FUQFHQFGJJOZAS-UHFFFAOYSA-N 0.000 claims 1
- MHZJJAIGKMPBFH-UHFFFAOYSA-N 4-[4-(8-methoxynaphthalen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2C(OC)=CC=CC2=CC=C1C(C1=CC=2)CN(C)CC1=CC=2N1CCOCC1 MHZJJAIGKMPBFH-UHFFFAOYSA-N 0.000 claims 1
- MUAQJAMKMHILIH-UHFFFAOYSA-N 4-[5-fluoro-4-(1h-indazol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=NNC4=CC=3)C2=C(F)C=C1N1CCOCC1 MUAQJAMKMHILIH-UHFFFAOYSA-N 0.000 claims 1
- YOIATGAJPXQHIX-UHFFFAOYSA-N 4-[5-fluoro-4-(1h-indazol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4NN=CC4=CC=3)C2=C(F)C=C1N1CCOCC1 YOIATGAJPXQHIX-UHFFFAOYSA-N 0.000 claims 1
- NSYSJDVYZWFTFN-UHFFFAOYSA-N 4-[5-fluoro-4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=C(F)C=C1N1CCOCC1 NSYSJDVYZWFTFN-UHFFFAOYSA-N 0.000 claims 1
- GWFNPVVSDSBLNP-UHFFFAOYSA-N 4-[6-(2-methyl-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinolin-7-yl)pyridazin-3-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C(N=N1)=CC=C1N1CCOCC1 GWFNPVVSDSBLNP-UHFFFAOYSA-N 0.000 claims 1
- HWFMXNVGXWAOOP-UHFFFAOYSA-N 4-[6-[4-(1-benzothiophen-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]pyridazin-3-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C(N=N1)=CC=C1N1CCOCC1 HWFMXNVGXWAOOP-UHFFFAOYSA-N 0.000 claims 1
- ZXGQFKTZKYLDPG-UHFFFAOYSA-N 4-[6-[4-(1-benzothiophen-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]pyridazin-3-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4SC=CC4=CC=3)C2=CC=C1C(N=N1)=CC=C1N1CCOCC1 ZXGQFKTZKYLDPG-UHFFFAOYSA-N 0.000 claims 1
- NJSNXHYNHMUTSO-UHFFFAOYSA-N 4-[6-[4-(1h-indazol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]pyridazin-3-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=NNC4=CC=3)C2=CC=C1C(N=N1)=CC=C1N1CCOCC1 NJSNXHYNHMUTSO-UHFFFAOYSA-N 0.000 claims 1
- LNZVVQUQTNMPPD-UHFFFAOYSA-N 4-[6-[4-(1h-indazol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]pyridazin-3-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4NN=CC4=CC=3)C2=CC=C1C(N=N1)=CC=C1N1CCOCC1 LNZVVQUQTNMPPD-UHFFFAOYSA-N 0.000 claims 1
- JWYVNLXDWJIJBQ-UHFFFAOYSA-N 4-[6-[4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]pyridazin-3-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1C(N=N1)=CC=C1N1CCOCC1 JWYVNLXDWJIJBQ-UHFFFAOYSA-N 0.000 claims 1
- WVNHIMUJJLODCU-UHFFFAOYSA-N 4-[6-[4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]pyridazin-3-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CNC4=CC=3)C2=CC=C1C(N=N1)=CC=C1N1CCOCC1 WVNHIMUJJLODCU-UHFFFAOYSA-N 0.000 claims 1
- FYDWWWLYQFIDLG-UHFFFAOYSA-N 4-[6-fluoro-4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC(F)=C1N1CCOCC1 FYDWWWLYQFIDLG-UHFFFAOYSA-N 0.000 claims 1
- IZRVMNFZJKPNFV-UHFFFAOYSA-N 4-[6-fluoro-4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CNC4=CC=3)C2=CC(F)=C1N1CCOCC1 IZRVMNFZJKPNFV-UHFFFAOYSA-N 0.000 claims 1
- OOCMXUDNXMNVNT-UHFFFAOYSA-N 4-[6-fluoro-4-(1h-indol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4NC=CC4=CC=3)C2=CC(F)=C1N1CCOCC1 OOCMXUDNXMNVNT-UHFFFAOYSA-N 0.000 claims 1
- HBROYWYVRWGNDV-UHFFFAOYSA-N 4-[8-fluoro-4-(1h-indazol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound FC1=C2CN(C)CC(C=3C=C4C=NNC4=CC=3)C2=CC=C1N1CCOCC1 HBROYWYVRWGNDV-UHFFFAOYSA-N 0.000 claims 1
- HVDFOSUNLCGUGQ-UHFFFAOYSA-N 4-[8-fluoro-4-(1h-indazol-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound FC1=C2CN(C)CC(C=3C=C4NN=CC4=CC=3)C2=CC=C1N1CCOCC1 HVDFOSUNLCGUGQ-UHFFFAOYSA-N 0.000 claims 1
- UVAAMDOYXLXFHX-UHFFFAOYSA-N 4-[8-fluoro-4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound FC1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1N1CCOCC1 UVAAMDOYXLXFHX-UHFFFAOYSA-N 0.000 claims 1
- KRVQPLSNNHDGSH-UHFFFAOYSA-N 4-[8-fluoro-4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound FC1=C2CN(C)CC(C=3C=C4C=CNC4=CC=3)C2=CC=C1N1CCOCC1 KRVQPLSNNHDGSH-UHFFFAOYSA-N 0.000 claims 1
- QMOZFCXYKWWVFV-UHFFFAOYSA-N 4-[[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]methyl]morpholine Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1CN1CCOCC1 QMOZFCXYKWWVFV-UHFFFAOYSA-N 0.000 claims 1
- MERYYVNEHMWPRO-UHFFFAOYSA-N 4-chloro-2-methyl-4-naphthalen-2-yl-1,3-dihydroisoquinoline Chemical compound C1=CC=CC2=CC(C3(Cl)C4=CC=CC=C4CN(C3)C)=CC=C21 MERYYVNEHMWPRO-UHFFFAOYSA-N 0.000 claims 1
- KAKUVLHTQPYEKV-UHFFFAOYSA-N 4-chloro-4-(1h-indol-5-yl)-2-methyl-1,3-dihydroisoquinoline Chemical compound C1=C2NC=CC2=CC(C2(Cl)C3=CC=CC=C3CN(C2)C)=C1 KAKUVLHTQPYEKV-UHFFFAOYSA-N 0.000 claims 1
- QFRQVPCZZDWGSH-UHFFFAOYSA-N 4-fluoro-4-(1h-indol-2-yl)-2-methyl-1,3-dihydroisoquinoline Chemical compound C1=CC=C2NC(C3(F)C4=CC=CC=C4CN(C3)C)=CC2=C1 QFRQVPCZZDWGSH-UHFFFAOYSA-N 0.000 claims 1
- BVRQJRCGIDVKOU-UHFFFAOYSA-N 4-fluoro-4-(1h-indol-6-yl)-2-methyl-1,3-dihydroisoquinoline Chemical compound C1=C2C=CNC2=CC(C2(F)C3=CC=CC=C3CN(C2)C)=C1 BVRQJRCGIDVKOU-UHFFFAOYSA-N 0.000 claims 1
- WANRCRILORHLCV-UHFFFAOYSA-N 4-imidazo[1,2-a]pyridin-6-yl-2-methyl-1-piperidin-1-yl-3,4-dihydro-1h-isoquinoline Chemical compound CN1CC(C2=CN3C=CN=C3C=C2)C2=CC=CC=C2C1N1CCCCC1 WANRCRILORHLCV-UHFFFAOYSA-N 0.000 claims 1
- JMTTXCLECVXOQH-UHFFFAOYSA-N 4-imidazo[1,2-a]pyridin-6-yl-2-methyl-1-pyrrolidin-1-yl-3,4-dihydro-1h-isoquinoline Chemical compound CN1CC(C2=CN3C=CN=C3C=C2)C2=CC=CC=C2C1N1CCCC1 JMTTXCLECVXOQH-UHFFFAOYSA-N 0.000 claims 1
- ISHDSKIZMZANIH-UHFFFAOYSA-N 4-imidazo[1,2-a]pyridin-7-yl-2-methyl-7-pyrrolidin-1-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C3=CC4=NC=CN4C=C3)C2=CC=C1N1CCCC1 ISHDSKIZMZANIH-UHFFFAOYSA-N 0.000 claims 1
- HHJMJXDDUGMTMZ-UHFFFAOYSA-N 4-indazol-1-yl-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound N1=CC2=CC=CC=C2N1C1CN(C)CC2=CC=CC=C21 HHJMJXDDUGMTMZ-UHFFFAOYSA-N 0.000 claims 1
- VGMBBROINOZNNC-UHFFFAOYSA-N 4-methoxy-2-methyl-4-naphthalen-2-yl-1,3-dihydroisoquinoline Chemical compound C1=CC=CC2=CC(C3(C4=CC=CC=C4CN(C)C3)OC)=CC=C21 VGMBBROINOZNNC-UHFFFAOYSA-N 0.000 claims 1
- CYMBOKBREHKYJY-UHFFFAOYSA-N 4-naphthalen-2-yl-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=CC2=CC(C3C4=CC=CC=C4CNC3)=CC=C21 CYMBOKBREHKYJY-UHFFFAOYSA-N 0.000 claims 1
- MFRANVUFMGATJT-UHFFFAOYSA-N 5-(2-ethyl-3,4-dihydro-1h-isoquinolin-4-yl)-1-benzothiophen-4-ol Chemical compound C1=C2SC=CC2=C(O)C(C2CN(CC3=CC=CC=C32)CC)=C1 MFRANVUFMGATJT-UHFFFAOYSA-N 0.000 claims 1
- MXWHZWJAUNVKQH-UHFFFAOYSA-N 5-(2-methyl-1-morpholin-4-yl-3,4-dihydro-1h-isoquinolin-4-yl)-1,3-benzoxazole Chemical compound CN1CC(C=2C=C3N=COC3=CC=2)C2=CC=CC=C2C1N1CCOCC1 MXWHZWJAUNVKQH-UHFFFAOYSA-N 0.000 claims 1
- RCXXCLNWXWQMSS-UHFFFAOYSA-N 5-(2-methyl-1-piperidin-1-yl-3,4-dihydro-1h-isoquinolin-4-yl)-1,3-benzothiazole Chemical compound CN1CC(C=2C=C3N=CSC3=CC=2)C2=CC=CC=C2C1N1CCCCC1 RCXXCLNWXWQMSS-UHFFFAOYSA-N 0.000 claims 1
- BBTFAIVVLKXFSF-UHFFFAOYSA-N 5-(2-methyl-1-piperidin-1-yl-3,4-dihydro-1h-isoquinolin-4-yl)-1,3-benzoxazole Chemical compound CN1CC(C=2C=C3N=COC3=CC=2)C2=CC=CC=C2C1N1CCCCC1 BBTFAIVVLKXFSF-UHFFFAOYSA-N 0.000 claims 1
- HVGZZFMGVNQEGP-UHFFFAOYSA-N 5-(2-methyl-1-pyrrolidin-1-yl-3,4-dihydro-1h-isoquinolin-4-yl)-1,2-benzothiazole Chemical compound CN1CC(C=2C=C3C=NSC3=CC=2)C2=CC=CC=C2C1N1CCCC1 HVGZZFMGVNQEGP-UHFFFAOYSA-N 0.000 claims 1
- WIAOICDLWRIIAF-UHFFFAOYSA-N 5-(2-methyl-1-pyrrolidin-1-yl-3,4-dihydro-1h-isoquinolin-4-yl)-1,3-benzothiazole Chemical compound CN1CC(C=2C=C3N=CSC3=CC=2)C2=CC=CC=C2C1N1CCCC1 WIAOICDLWRIIAF-UHFFFAOYSA-N 0.000 claims 1
- IDMVCKYGKYRBQQ-UHFFFAOYSA-N 5-(2-methyl-1-pyrrolidin-1-yl-3,4-dihydro-1h-isoquinolin-4-yl)-1,3-benzoxazole Chemical compound CN1CC(C=2C=C3N=COC3=CC=2)C2=CC=CC=C2C1N1CCCC1 IDMVCKYGKYRBQQ-UHFFFAOYSA-N 0.000 claims 1
- AFLKYZDRMAFANE-UHFFFAOYSA-N 5-(2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)-1,2-benzoxazole Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=C(ON=C2)C2=C1 AFLKYZDRMAFANE-UHFFFAOYSA-N 0.000 claims 1
- JBZVMMXAKJXHTD-UHFFFAOYSA-N 5-methyl-2-(2-methyl-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinolin-7-yl)-1,3-thiazole Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=NC=C(C)S1 JBZVMMXAKJXHTD-UHFFFAOYSA-N 0.000 claims 1
- RVORBFYDPSSSSZ-UHFFFAOYSA-N 6-(2-methyl-1-morpholin-4-yl-3,4-dihydro-1h-isoquinolin-4-yl)-1,3-benzoxazole Chemical compound CN1CC(C=2C=C3OC=NC3=CC=2)C2=CC=CC=C2C1N1CCOCC1 RVORBFYDPSSSSZ-UHFFFAOYSA-N 0.000 claims 1
- CUXOMJZENXBQPH-UHFFFAOYSA-N 6-(2-methyl-1-piperidin-1-yl-3,4-dihydro-1h-isoquinolin-4-yl)-1,2-benzothiazole Chemical compound CN1CC(C=2C=C3SN=CC3=CC=2)C2=CC=CC=C2C1N1CCCCC1 CUXOMJZENXBQPH-UHFFFAOYSA-N 0.000 claims 1
- KOKROGZRDUDWFJ-UHFFFAOYSA-N 6-(2-methyl-1-piperidin-1-yl-3,4-dihydro-1h-isoquinolin-4-yl)-1,3-benzothiazole Chemical compound CN1CC(C=2C=C3SC=NC3=CC=2)C2=CC=CC=C2C1N1CCCCC1 KOKROGZRDUDWFJ-UHFFFAOYSA-N 0.000 claims 1
- XTAIMLJCARPOCI-UHFFFAOYSA-N 6-(2-methyl-1-piperidin-1-yl-3,4-dihydro-1h-isoquinolin-4-yl)-1,3-benzoxazole Chemical compound CN1CC(C=2C=C3OC=NC3=CC=2)C2=CC=CC=C2C1N1CCCCC1 XTAIMLJCARPOCI-UHFFFAOYSA-N 0.000 claims 1
- XXPUQCVVNKOBQY-UHFFFAOYSA-N 6-(2-methyl-1-pyrrolidin-1-yl-3,4-dihydro-1h-isoquinolin-4-yl)-1,2-benzothiazole Chemical compound CN1CC(C=2C=C3SN=CC3=CC=2)C2=CC=CC=C2C1N1CCCC1 XXPUQCVVNKOBQY-UHFFFAOYSA-N 0.000 claims 1
- MTVVOQALHCFGHW-UHFFFAOYSA-N 6-(2-methyl-1-pyrrolidin-1-yl-3,4-dihydro-1h-isoquinolin-4-yl)-1,3-benzothiazole Chemical compound CN1CC(C=2C=C3SC=NC3=CC=2)C2=CC=CC=C2C1N1CCCC1 MTVVOQALHCFGHW-UHFFFAOYSA-N 0.000 claims 1
- LIJKOAGATWSTTB-UHFFFAOYSA-N 6-(2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)quinazoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=C(N=CN=C2)C2=C1 LIJKOAGATWSTTB-UHFFFAOYSA-N 0.000 claims 1
- WXJVSDNWZOTTOK-UHFFFAOYSA-N 6-(2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)quinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=C(N=CC=C2)C2=C1 WXJVSDNWZOTTOK-UHFFFAOYSA-N 0.000 claims 1
- VCIBGDSRPUOBOG-UHFFFAOYSA-N 6-(2-methyl-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinolin-7-yl)pyridazin-3-amine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=CC=C(N)N=N1 VCIBGDSRPUOBOG-UHFFFAOYSA-N 0.000 claims 1
- QHYVWAVOJISKSH-UHFFFAOYSA-N 6-(2-methyl-7-piperidin-1-yl-3,4-dihydro-1h-isoquinolin-4-yl)quinazoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=NC=NC4=CC=3)C2=CC=C1N1CCCCC1 QHYVWAVOJISKSH-UHFFFAOYSA-N 0.000 claims 1
- NVRHNCICQHZPCU-UHFFFAOYSA-N 6-(2-methyl-7-piperidin-1-yl-3,4-dihydro-1h-isoquinolin-4-yl)thieno[2,3-b]pyridine Chemical compound C1=C2CN(C)CC(C=3N=C4SC=CC4=CC=3)C2=CC=C1N1CCCCC1 NVRHNCICQHZPCU-UHFFFAOYSA-N 0.000 claims 1
- LDQQHLNXULMMMY-UHFFFAOYSA-N 6-(2-methyl-7-piperidin-1-yl-3,4-dihydro-1h-isoquinolin-4-yl)thieno[3,2-b]pyridine Chemical compound C1=C2CN(C)CC(C=3C=C4SC=CC4=NC=3)C2=CC=C1N1CCCCC1 LDQQHLNXULMMMY-UHFFFAOYSA-N 0.000 claims 1
- GHHOPLSSKDPCRI-UHFFFAOYSA-N 6-(2-methyl-7-pyrrolidin-1-yl-3,4-dihydro-1h-isoquinolin-4-yl)quinoxaline Chemical compound C1=C2CN(C)CC(C=3C=C4N=CC=NC4=CC=3)C2=CC=C1N1CCCC1 GHHOPLSSKDPCRI-UHFFFAOYSA-N 0.000 claims 1
- WBJQADJFBRMBAU-UHFFFAOYSA-N 6-(7-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)quinoline Chemical compound N1=CC=CC2=CC(C3C4=CC=C(C=C4CN(C)C3)OC)=CC=C21 WBJQADJFBRMBAU-UHFFFAOYSA-N 0.000 claims 1
- VQGSMASLNNYQAO-UHFFFAOYSA-N 6-[4-(1-benzofuran-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n,n-dimethylpyridazin-3-amine Chemical compound N1=NC(N(C)C)=CC=C1C1=CC=C(C(CN(C)C2)C=3OC4=CC=CC=C4C=3)C2=C1 VQGSMASLNNYQAO-UHFFFAOYSA-N 0.000 claims 1
- DZPNBKZGXNRNQK-UHFFFAOYSA-N 6-[4-(1-benzofuran-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n-methylpyridazin-3-amine Chemical compound N1=NC(NC)=CC=C1C1=CC=C(C(CN(C)C2)C=3OC4=CC=CC=C4C=3)C2=C1 DZPNBKZGXNRNQK-UHFFFAOYSA-N 0.000 claims 1
- AUOQKKJAXNPUIK-UHFFFAOYSA-N 6-[4-(1-benzofuran-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]pyridazin-3-amine Chemical compound C1=C2CN(C)CC(C=3OC4=CC=CC=C4C=3)C2=CC=C1C1=CC=C(N)N=N1 AUOQKKJAXNPUIK-UHFFFAOYSA-N 0.000 claims 1
- QXLYIFRIUDHMIF-UHFFFAOYSA-N 6-[4-(1-benzofuran-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]pyridazine-3-carbonitrile Chemical compound C1=C2CN(C)CC(C=3OC4=CC=CC=C4C=3)C2=CC=C1C1=CC=C(C#N)N=N1 QXLYIFRIUDHMIF-UHFFFAOYSA-N 0.000 claims 1
- FQAWJTNKDJDGOC-UHFFFAOYSA-N 6-[4-(1-benzofuran-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]pyridazine-3-carbonitrile Chemical compound C1=C2CN(C)CC(C=3C=C4C=COC4=CC=3)C2=CC=C1C1=CC=C(C#N)N=N1 FQAWJTNKDJDGOC-UHFFFAOYSA-N 0.000 claims 1
- BLVWTSPQQTXRMT-UHFFFAOYSA-N 6-[4-(1-benzothiophen-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]quinazoline Chemical compound N1=CN=CC2=CC(C3=CC=C4C(C=5C=C6C=CSC6=CC=5)CN(CC4=C3)C)=CC=C21 BLVWTSPQQTXRMT-UHFFFAOYSA-N 0.000 claims 1
- QSGNNIBDLVIYCK-UHFFFAOYSA-N 6-[4-(1-benzothiophen-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n,n-dimethylpyridazin-3-amine Chemical compound N1=NC(N(C)C)=CC=C1C1=CC=C(C(CN(C)C2)C=3C=C4SC=CC4=CC=3)C2=C1 QSGNNIBDLVIYCK-UHFFFAOYSA-N 0.000 claims 1
- NUCFBKDZDOZKAD-UHFFFAOYSA-N 6-[4-(1-benzothiophen-6-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]quinazoline Chemical compound N1=CN=CC2=CC(C3=CC=C4C(C=5C=C6SC=CC6=CC=5)CN(CC4=C3)C)=CC=C21 NUCFBKDZDOZKAD-UHFFFAOYSA-N 0.000 claims 1
- DJWZZQRMPOIMSP-UHFFFAOYSA-N 6-[4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]pyridazin-3-amine Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1C1=CC=C(N)N=N1 DJWZZQRMPOIMSP-UHFFFAOYSA-N 0.000 claims 1
- KINKWVZGKYECPG-UHFFFAOYSA-N 6-[4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]pyridazine-3-carbonitrile Chemical compound C1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1C1=CC=C(C#N)N=N1 KINKWVZGKYECPG-UHFFFAOYSA-N 0.000 claims 1
- YZLHMGLVROSFOH-UHFFFAOYSA-N 6-[4-(1h-indol-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]quinazoline Chemical compound N1=CN=CC2=CC(C3=CC=C4C(C=5NC6=CC=CC=C6C=5)CN(CC4=C3)C)=CC=C21 YZLHMGLVROSFOH-UHFFFAOYSA-N 0.000 claims 1
- LCQPOBUOXROJNE-UHFFFAOYSA-N 6-[4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]pyridazin-3-amine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CNC4=CC=3)C2=CC=C1C1=CC=C(N)N=N1 LCQPOBUOXROJNE-UHFFFAOYSA-N 0.000 claims 1
- DEVXZGOVZAWZSU-UHFFFAOYSA-N 6-[4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]pyridazine-3-carbonitrile Chemical compound C1=C2CN(C)CC(C=3C=C4C=CNC4=CC=3)C2=CC=C1C1=CC=C(C#N)N=N1 DEVXZGOVZAWZSU-UHFFFAOYSA-N 0.000 claims 1
- RPLSWSGQDXJVRK-UHFFFAOYSA-N 6-[4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]quinazoline Chemical compound N1=CN=CC2=CC(C3=CC=C4C(C=5C=C6C=CNC6=CC=5)CN(CC4=C3)C)=CC=C21 RPLSWSGQDXJVRK-UHFFFAOYSA-N 0.000 claims 1
- SMHBPWAIPUNVLC-UHFFFAOYSA-N 6-fluoro-2-methyl-4-naphthalen-2-yl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC(F)=C1C1=CC=CN=N1 SMHBPWAIPUNVLC-UHFFFAOYSA-N 0.000 claims 1
- MWFSWNIXXBUXDU-UHFFFAOYSA-N 7-(2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)-1,2-benzoxazole Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=CC2=C1ON=C2 MWFSWNIXXBUXDU-UHFFFAOYSA-N 0.000 claims 1
- JOTAFSSSCBSWLY-UHFFFAOYSA-N 7-(3-methoxypyrazin-2-yl)-2-methyl-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=NC=CN=C1C1=CC=C(C(CN(C)C2)C=3C=C4C=CC=CC4=CC=3)C2=C1 JOTAFSSSCBSWLY-UHFFFAOYSA-N 0.000 claims 1
- RPPBJSZAIIRZBP-UHFFFAOYSA-N 7-[4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]quinazoline Chemical compound C1=NC=NC2=CC(C3=CC=C4C(C=5C=C6C=CNC6=CC=5)CN(CC4=C3)C)=CC=C21 RPPBJSZAIIRZBP-UHFFFAOYSA-N 0.000 claims 1
- WPCSQSMSSNPKKB-UHFFFAOYSA-N 7-fluoro-1-benzofuran Chemical compound FC1=CC=CC2=C1OC=C2 WPCSQSMSSNPKKB-UHFFFAOYSA-N 0.000 claims 1
- VWXUWQQIEGFMTM-UHFFFAOYSA-N 7-fluoro-2-methyl-4-(1-methylindazol-6-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=C(F)C=C2CN(C)CC1C1=CC=C(C=NN2C)C2=C1 VWXUWQQIEGFMTM-UHFFFAOYSA-N 0.000 claims 1
- JTXRSABWWRDMBE-UHFFFAOYSA-N 7-fluoro-2-methyl-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=C(F)C=C2CN(C)CC1C1=CC=C(C=CC=C2)C2=C1 JTXRSABWWRDMBE-UHFFFAOYSA-N 0.000 claims 1
- BEKHMUJHFZAIQP-UHFFFAOYSA-N 7-fluoro-4-(1h-indol-5-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=C(F)C=C2CN(C)CC1C1=CC=C(NC=C2)C2=C1 BEKHMUJHFZAIQP-UHFFFAOYSA-N 0.000 claims 1
- FZPCCSSMXFFDEE-UHFFFAOYSA-N 7-methoxy-2-methyl-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=CC=CC2=CC(C3C4=CC=C(C=C4CN(C)C3)OC)=CC=C21 FZPCCSSMXFFDEE-UHFFFAOYSA-N 0.000 claims 1
- CQVWTBQVQQBJGC-UHFFFAOYSA-N 8-fluoro-2-methyl-4-(1-methylindol-5-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC(F)=C2CN(C)CC1C1=CC=C(N(C)C=C2)C2=C1 CQVWTBQVQQBJGC-UHFFFAOYSA-N 0.000 claims 1
- VGCVAPVUYYHRLU-UHFFFAOYSA-N 8-fluoro-2-methyl-4-(1-methylindol-6-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC(F)=C2CN(C)CC1C1=CC=C(C=CN2C)C2=C1 VGCVAPVUYYHRLU-UHFFFAOYSA-N 0.000 claims 1
- NYKAWOCNCNBQBJ-UHFFFAOYSA-N 8-fluoro-2-methyl-4-naphthalen-2-yl-3,4-dihydro-1h-isoquinoline-7-carbonitrile Chemical compound C12=CC=C(C#N)C(F)=C2CN(C)CC1C1=CC=C(C=CC=C2)C2=C1 NYKAWOCNCNBQBJ-UHFFFAOYSA-N 0.000 claims 1
- BHHKQLFZVSNOGW-UHFFFAOYSA-N 8-fluoro-2-methyl-4-naphthalen-2-yl-7-pyrazin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=CN=CC=N1 BHHKQLFZVSNOGW-UHFFFAOYSA-N 0.000 claims 1
- WYIOBNTYUBBSOS-UHFFFAOYSA-N 8-fluoro-2-methyl-4-naphthalen-2-yl-7-pyridazin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=CC=NN=C1 WYIOBNTYUBBSOS-UHFFFAOYSA-N 0.000 claims 1
- BQTBNLXIZUYGCR-UHFFFAOYSA-N 8-fluoro-2-methyl-4-naphthalen-2-yl-7-pyrimidin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=NC=CC=N1 BQTBNLXIZUYGCR-UHFFFAOYSA-N 0.000 claims 1
- NFDXOTNUDNIDKV-UHFFFAOYSA-N 8-fluoro-2-methyl-4-naphthalen-2-yl-7-pyrimidin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=CC=NC=N1 NFDXOTNUDNIDKV-UHFFFAOYSA-N 0.000 claims 1
- OOXWAQPCOLHIRF-UHFFFAOYSA-N 8-fluoro-2-methyl-4-naphthalen-2-yl-7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=CN=CN=C1 OOXWAQPCOLHIRF-UHFFFAOYSA-N 0.000 claims 1
- UUIRQEWIUREWOD-UHFFFAOYSA-N 8-fluoro-4-(1h-indol-2-yl)-2-methyl-7-pyridazin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1C1=CC=NN=C1 UUIRQEWIUREWOD-UHFFFAOYSA-N 0.000 claims 1
- NSFBWOTWNGDANE-UHFFFAOYSA-N 8-fluoro-4-(1h-indol-2-yl)-2-methyl-7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3NC4=CC=CC=C4C=3)C2=CC=C1C1=CN=CN=C1 NSFBWOTWNGDANE-UHFFFAOYSA-N 0.000 claims 1
- OZIWXEAYHUENFO-UHFFFAOYSA-N 8-fluoro-4-(1h-indol-5-yl)-2-methyl-7-pyridazin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3C=C4C=CNC4=CC=3)C2=CC=C1C1=CC=NN=C1 OZIWXEAYHUENFO-UHFFFAOYSA-N 0.000 claims 1
- JUXHWBAAFOAXSV-UHFFFAOYSA-N 8-fluoro-4-(1h-indol-6-yl)-2-methyl-7-pyridazin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3C=C4NC=CC4=CC=3)C2=CC=C1C1=CC=NN=C1 JUXHWBAAFOAXSV-UHFFFAOYSA-N 0.000 claims 1
- AVEXDBJZFHPQLV-UHFFFAOYSA-N 8-fluoro-4-(1h-indol-6-yl)-2-methyl-7-pyrimidin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3C=C4NC=CC4=CC=3)C2=CC=C1C1=CC=NC=N1 AVEXDBJZFHPQLV-UHFFFAOYSA-N 0.000 claims 1
- PTOQOFSBIQYIMZ-UHFFFAOYSA-N 8-fluoro-4-(4-methoxy-1-benzothiophen-5-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=CC=2SC=CC=2C(OC)=C1C(C1=CC=2)CN(C)CC1=C(F)C=2C1=CC=CN=N1 PTOQOFSBIQYIMZ-UHFFFAOYSA-N 0.000 claims 1
- FBTXUNUXFNTBCZ-UHFFFAOYSA-N 8-methoxy-2-methyl-4-naphthalen-2-yl-7-pyrazin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=CN=CC=N1 FBTXUNUXFNTBCZ-UHFFFAOYSA-N 0.000 claims 1
- DWNTVSDKHBIXPF-UHFFFAOYSA-N 8-methoxy-2-methyl-4-naphthalen-2-yl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=CC=CN=N1 DWNTVSDKHBIXPF-UHFFFAOYSA-N 0.000 claims 1
- ZBAYQXKCGKPWPP-UHFFFAOYSA-N 8-methoxy-2-methyl-4-naphthalen-2-yl-7-pyrimidin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=NC=CC=N1 ZBAYQXKCGKPWPP-UHFFFAOYSA-N 0.000 claims 1
- FCKNBESFZKBKQS-UHFFFAOYSA-N 8-methoxy-2-methyl-4-naphthalen-2-yl-7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=C2CN(C)CC(C=3C=C4C=CC=CC4=CC=3)C2=CC=C1C1=CN=CN=C1 FCKNBESFZKBKQS-UHFFFAOYSA-N 0.000 claims 1
- 208000007848 Alcoholism Diseases 0.000 claims 1
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 1
- 206010006550 Bulimia nervosa Diseases 0.000 claims 1
- XGDDAJKEDQGDNH-UHFFFAOYSA-N CC1=C(C(C2=CC(C=CC=C3)=C3O2)N(C)CC2)C2=CC=C1C1=CC=CN=N1 Chemical compound CC1=C(C(C2=CC(C=CC=C3)=C3O2)N(C)CC2)C2=CC=C1C1=CC=CN=N1 XGDDAJKEDQGDNH-UHFFFAOYSA-N 0.000 claims 1
- WJBKSSJCSQFNQE-UHFFFAOYSA-N CN1CC(c2ccc(cc2C1)N1CCOCC1)c1c(ccc2ccccc12)C#N Chemical compound CN1CC(c2ccc(cc2C1)N1CCOCC1)c1c(ccc2ccccc12)C#N WJBKSSJCSQFNQE-UHFFFAOYSA-N 0.000 claims 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 1
- 208000027776 Extrapyramidal disease Diseases 0.000 claims 1
- 101000831616 Homo sapiens Protachykinin-1 Proteins 0.000 claims 1
- 208000033830 Hot Flashes Diseases 0.000 claims 1
- 206010060800 Hot flush Diseases 0.000 claims 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-Tyrosine Natural products OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 1
- 125000003798 L-tyrosyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C([H])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 1
- 208000009625 Lesch-Nyhan syndrome Diseases 0.000 claims 1
- WKSXRWSOSLGSTN-UHFFFAOYSA-N Methoxypyrazine Chemical group COC1=CN=CC=N1 WKSXRWSOSLGSTN-UHFFFAOYSA-N 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- UMTDAKAAYOXIKU-UHFFFAOYSA-N N-tert-butyl-3-[4-(2-methoxyphenyl)-1-piperazinyl]-2-phenylpropanamide Chemical compound COC1=CC=CC=C1N1CCN(CC(C(=O)NC(C)(C)C)C=2C=CC=CC=2)CC1 UMTDAKAAYOXIKU-UHFFFAOYSA-N 0.000 claims 1
- 206010034912 Phobia Diseases 0.000 claims 1
- 102100024304 Protachykinin-1 Human genes 0.000 claims 1
- 206010048327 Supranuclear palsy Diseases 0.000 claims 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims 1
- 208000035317 Total hypoxanthine-guanine phosphoribosyl transferase deficiency Diseases 0.000 claims 1
- 208000031674 Traumatic Acute Stress disease Diseases 0.000 claims 1
- AYSYSOQSKKDJJY-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]pyridine Chemical compound C1=CC=CN2C=NN=C21 AYSYSOQSKKDJJY-UHFFFAOYSA-N 0.000 claims 1
- 208000026345 acute stress disease Diseases 0.000 claims 1
- 230000036592 analgesia Effects 0.000 claims 1
- 239000003420 antiserotonin agent Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000019771 cognition Effects 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 208000013403 hyperactivity Diseases 0.000 claims 1
- 125000004536 indazol-1-yl group Chemical group N1(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 claims 1
- 230000029849 luteinization Effects 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 229960002715 nicotine Drugs 0.000 claims 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 1
- 230000000422 nocturnal effect Effects 0.000 claims 1
- 229960005190 phenylalanine Drugs 0.000 claims 1
- 206010036596 premature ejaculation Diseases 0.000 claims 1
- 229940121356 serotonin receptor antagonist Drugs 0.000 claims 1
- 201000001716 specific phobia Diseases 0.000 claims 1
- DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 claims 1
- 229950001675 spiperone Drugs 0.000 claims 1
- ADNPLDHMAVUMIW-CUZNLEPHSA-N substance P Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CCCN=C(N)N)C1=CC=CC=C1 ADNPLDHMAVUMIW-CUZNLEPHSA-N 0.000 claims 1
- 208000016686 tic disease Diseases 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 claims 1
- 229960004441 tyrosine Drugs 0.000 claims 1
- 230000000694 effects Effects 0.000 description 12
- 239000003814 drug Substances 0.000 description 11
- 229940079593 drug Drugs 0.000 description 10
- 229940002612 prodrug Drugs 0.000 description 10
- 239000000651 prodrug Substances 0.000 description 10
- 239000000935 antidepressant agent Substances 0.000 description 9
- 229940005513 antidepressants Drugs 0.000 description 9
- VHGCDTVCOLNTBX-QGZVFWFLSA-N atomoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=CC=C1C VHGCDTVCOLNTBX-QGZVFWFLSA-N 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 102000019208 Serotonin Plasma Membrane Transport Proteins Human genes 0.000 description 8
- 108010012996 Serotonin Plasma Membrane Transport Proteins Proteins 0.000 description 8
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 7
- 229960002430 atomoxetine Drugs 0.000 description 7
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 7
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 7
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 7
- 102000006441 Dopamine Plasma Membrane Transport Proteins Human genes 0.000 description 6
- 108010044266 Dopamine Plasma Membrane Transport Proteins Proteins 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 6
- PRTRSEDVLBBFJZ-UHFFFAOYSA-N 1-phenyl-1,2,3,4-tetrahydroisoquinoline Chemical class N1CCC2=CC=CC=C2C1C1=CC=CC=C1 PRTRSEDVLBBFJZ-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- 229940124639 Selective inhibitor Drugs 0.000 description 5
- 230000001430 anti-depressive effect Effects 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000460 chlorine Chemical group 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- ZEUITGRIYCTCEM-KRWDZBQOSA-N (S)-duloxetine Chemical compound C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 ZEUITGRIYCTCEM-KRWDZBQOSA-N 0.000 description 4
- 108010078791 Carrier Proteins Proteins 0.000 description 4
- 208000020401 Depressive disease Diseases 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229960002866 duloxetine Drugs 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000002858 neurotransmitter agent Substances 0.000 description 4
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 4
- 229960004688 venlafaxine Drugs 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- XXPANQJNYNUNES-UHFFFAOYSA-N nomifensine Chemical compound C12=CC=CC(N)=C2CN(C)CC1C1=CC=CC=C1 XXPANQJNYNUNES-UHFFFAOYSA-N 0.000 description 3
- 229960001073 nomifensine Drugs 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical class CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000004475 Arginine Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229940123821 Neurokinin 1 receptor antagonist Drugs 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 102100034333 Synaptic vesicular amine transporter Human genes 0.000 description 2
- 101710164184 Synaptic vesicular amine transporter Proteins 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 208000026935 allergic disease Diseases 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 239000003429 antifungal agent Substances 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
- 229960003121 arginine Drugs 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 208000015114 central nervous system disease Diseases 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 238000002648 combination therapy Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000009510 drug design Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229960003646 lysine Drugs 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- PFPSZGPAQFBVHZ-UHFFFAOYSA-N n-(3-chlorophenyl)-2-[(4-phenyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]acetamide Chemical compound ClC1=CC=CC(NC(=O)CSC=2N(C(C=3C=CN=CC=3)=NN=2)C=2C=CC=CC=2)=C1 PFPSZGPAQFBVHZ-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002742 neurokinin 1 receptor antagonist Substances 0.000 description 2
- 239000002767 noradrenalin uptake inhibitor Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000010452 phosphate Chemical class 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical class [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 229940012488 strattera Drugs 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Chemical class OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 description 1
- RHKPSKRYUUZBNP-UHFFFAOYSA-N 1-[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n,n-dimethylcyclopropan-1-amine Chemical compound C=1C=C2C(C=3SC4=CC=CC=C4C=3)CN(C)CC2=CC=1C1(N(C)C)CC1 RHKPSKRYUUZBNP-UHFFFAOYSA-N 0.000 description 1
- XJIGUEICACIGFU-UHFFFAOYSA-N 1-[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]cyclopropan-1-amine Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1C1(N)CC1 XJIGUEICACIGFU-UHFFFAOYSA-N 0.000 description 1
- MKZUFDMKLRVETP-UHFFFAOYSA-N 1-[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]phthalazine Chemical compound C1=CC=C2C(C3=CC=C4C(C=5SC6=CC=CC=C6C=5)CN(CC4=C3)C)=NN=CC2=C1 MKZUFDMKLRVETP-UHFFFAOYSA-N 0.000 description 1
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 1
- NTOIKDYVJIWVSU-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid Chemical class C1=CC(C)=CC=C1C(=O)C(O)(C(O)=O)C(O)(C(O)=O)C(=O)C1=CC=C(C)C=C1 NTOIKDYVJIWVSU-UHFFFAOYSA-N 0.000 description 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- CWVCGIBQWMDPOH-UHFFFAOYSA-N 2-(1,2,3,4-tetrahydroisoquinolin-4-yl)quinolin-3-ol Chemical compound C1NCC2=CC=CC=C2C1C1=NC2=CC=CC=C2C=C1O CWVCGIBQWMDPOH-UHFFFAOYSA-N 0.000 description 1
- ZDNTXXHEQINCGS-UHFFFAOYSA-N 2-[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-5-methyl-1,3-thiazole Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1C1=NC=C(C)S1 ZDNTXXHEQINCGS-UHFFFAOYSA-N 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- UEOVHGJVJKIGFD-UHFFFAOYSA-N 2-ethyl-4-(4-methoxy-1-benzothiophen-5-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2SC=CC2=C(OC)C(C2CN(CC3=CC=CC=C32)CC)=C1 UEOVHGJVJKIGFD-UHFFFAOYSA-N 0.000 description 1
- VMFUSLMJSZHTBN-UHFFFAOYSA-N 2-ethyl-4-(4-methoxy-1-benzothiophen-5-yl)-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(CC)CC(C=3C(=C4C=CSC4=CC=3)OC)C2=CC=C1C1=CC=CN=N1 VMFUSLMJSZHTBN-UHFFFAOYSA-N 0.000 description 1
- NFRZUWIBUDOOBK-UHFFFAOYSA-N 2-ethyl-8-fluoro-4-(4-methoxy-1-benzothiophen-5-yl)-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(CC)CC(C=3C(=C4C=CSC4=CC=3)OC)C2=CC=C1C1=CC=CN=N1 NFRZUWIBUDOOBK-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- VPQZKEHFLFBSMI-UHFFFAOYSA-N 2-methyl-7-pyrimidin-4-yl-4-[3-(trifluoromethyl)-1-benzothiophen-5-yl]-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C(=CSC4=CC=3)C(F)(F)F)C2=CC=C1C1=CC=NC=N1 VPQZKEHFLFBSMI-UHFFFAOYSA-N 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- BUFFHJOEBYHMPJ-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-2-ethyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(CC)CC1C1=CC2=CC=CC=C2S1 BUFFHJOEBYHMPJ-UHFFFAOYSA-N 0.000 description 1
- NBNCDBSNLRNANJ-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-2-ethyl-8-fluoro-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(CC)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1C1=CC=CN=N1 NBNCDBSNLRNANJ-UHFFFAOYSA-N 0.000 description 1
- CKAAFVYKIXKJMW-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-2-methyl-7-(3-methylpyrazin-2-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1C1=NC=CN=C1C CKAAFVYKIXKJMW-UHFFFAOYSA-N 0.000 description 1
- UFUGZEVPWFDBGL-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-2-methyl-7-(4-methylpiperazin-1-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1CN(C)CCN1C1=CC=C(C(CN(C)C2)C=3SC4=CC=CC=C4C=3)C2=C1 UFUGZEVPWFDBGL-UHFFFAOYSA-N 0.000 description 1
- ZLFYTLGWWZARCL-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-2-methyl-7-(pyrrolidin-1-ylmethyl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1CN1CCCC1 ZLFYTLGWWZARCL-UHFFFAOYSA-N 0.000 description 1
- IIIOJQHRQFOBDA-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-2-methyl-7-morpholin-4-yl-3,4-dihydro-1h-isoquinolin-8-ol Chemical compound OC1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1N1CCOCC1 IIIOJQHRQFOBDA-UHFFFAOYSA-N 0.000 description 1
- BQYUIIZKSMFLSU-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-2-methyl-7-piperazin-1-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1N1CCNCC1 BQYUIIZKSMFLSU-UHFFFAOYSA-N 0.000 description 1
- TXEMWLDZYFNSQR-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-2-methyl-7-pyridazin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1C1=CC=NN=C1 TXEMWLDZYFNSQR-UHFFFAOYSA-N 0.000 description 1
- JKQKHFJKKGCMPH-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-2-methyl-7-pyrimidin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1C1=CC=NC=N1 JKQKHFJKKGCMPH-UHFFFAOYSA-N 0.000 description 1
- HZIFLRKERKJFEH-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-4-fluoro-2-methyl-1,3-dihydroisoquinoline Chemical compound C1=CC=C2SC(C3(F)C4=CC=CC=C4CN(C3)C)=CC2=C1 HZIFLRKERKJFEH-UHFFFAOYSA-N 0.000 description 1
- CIIKISKMEWALBE-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-5-fluoro-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=C(F)C=C1C1=CC=CN=N1 CIIKISKMEWALBE-UHFFFAOYSA-N 0.000 description 1
- MAGVMOPIMJCLAU-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-6-fluoro-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC(F)=C1C1=CC=CN=N1 MAGVMOPIMJCLAU-UHFFFAOYSA-N 0.000 description 1
- KJWMUWCLVTWAMS-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-8-fluoro-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1C1=CC=CN=N1 KJWMUWCLVTWAMS-UHFFFAOYSA-N 0.000 description 1
- HRPQOATWRUHPIK-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-8-fluoro-2-methyl-7-pyridazin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1C1=CC=NN=C1 HRPQOATWRUHPIK-UHFFFAOYSA-N 0.000 description 1
- ZUISMTTUYDSFDL-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-8-fluoro-2-methyl-7-pyrimidin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1C1=NC=CC=N1 ZUISMTTUYDSFDL-UHFFFAOYSA-N 0.000 description 1
- HSZAOHWPQRYQSU-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-8-fluoro-2-methyl-7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1C1=CN=CN=C1 HSZAOHWPQRYQSU-UHFFFAOYSA-N 0.000 description 1
- QNHLHLIDSORULO-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-8-methoxy-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1C1=CC=CN=N1 QNHLHLIDSORULO-UHFFFAOYSA-N 0.000 description 1
- SAIMCZZUAXJQIZ-UHFFFAOYSA-N 4-(1-benzothiophen-4-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=4C=CSC=4C=CC=3)C2=CC=C1C1=CC=CN=N1 SAIMCZZUAXJQIZ-UHFFFAOYSA-N 0.000 description 1
- BHEURNSNXBSCQZ-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=C2SC=CC2=CC(C2C3=CC=CC=C3CNC2)=C1 BHEURNSNXBSCQZ-UHFFFAOYSA-N 0.000 description 1
- REOFSIYPYBMZAU-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2-ethyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(CC)CC1C1=CC=C(SC=C2)C2=C1 REOFSIYPYBMZAU-UHFFFAOYSA-N 0.000 description 1
- CZFRHEQYAMVYSG-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2-ethyl-8-fluoro-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(CC)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=CC=CN=N1 CZFRHEQYAMVYSG-UHFFFAOYSA-N 0.000 description 1
- LMORVABHZDICMT-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2-methyl-7-(6-methylpyrazin-2-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=CN=CC(C)=N1 LMORVABHZDICMT-UHFFFAOYSA-N 0.000 description 1
- YNUBEAWOGYUQLC-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2-methyl-7-[6-(trifluoromethyl)pyridazin-3-yl]-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=CC=C(C(F)(F)F)N=N1 YNUBEAWOGYUQLC-UHFFFAOYSA-N 0.000 description 1
- FDKOVAVNUWNHGD-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2-methyl-7-pyrimidin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=NC=CC=N1 FDKOVAVNUWNHGD-UHFFFAOYSA-N 0.000 description 1
- NBFQXZZGOZWFBY-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-2-methyl-7-pyrimidin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=CC=NC=N1 NBFQXZZGOZWFBY-UHFFFAOYSA-N 0.000 description 1
- VECKCLWOHKDDOQ-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-5-fluoro-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=C(F)C=C1C1=CC=CN=N1 VECKCLWOHKDDOQ-UHFFFAOYSA-N 0.000 description 1
- WFZNGVMUKZEZCR-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-7-(3-methoxypyrazin-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=NC=CN=C1C1=CC=C(C(CN(C)C2)C=3C=C4C=CSC4=CC=3)C2=C1 WFZNGVMUKZEZCR-UHFFFAOYSA-N 0.000 description 1
- DUQLBIXWABVDJL-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-8-fluoro-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC(F)=C2CN(C)CC1C1=CC=C(SC=C2)C2=C1 DUQLBIXWABVDJL-UHFFFAOYSA-N 0.000 description 1
- ZDFQTPWBDYCOSY-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-8-fluoro-2-methyl-7-pyrazin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=CN=CC=N1 ZDFQTPWBDYCOSY-UHFFFAOYSA-N 0.000 description 1
- VBIFZTGAGKUUEA-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-8-fluoro-2-methyl-7-pyridazin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=CC=NN=C1 VBIFZTGAGKUUEA-UHFFFAOYSA-N 0.000 description 1
- PPGKWDLMOBOQGM-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-8-fluoro-2-methyl-7-pyrimidin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=NC=CC=N1 PPGKWDLMOBOQGM-UHFFFAOYSA-N 0.000 description 1
- VRWADUSXLONQPU-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-8-fluoro-2-methyl-7-pyrimidin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound FC1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=CC=NC=N1 VRWADUSXLONQPU-UHFFFAOYSA-N 0.000 description 1
- XYJGSJOLIMTUEJ-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-8-methoxy-2-methyl-1,3-dihydroisoquinolin-4-ol Chemical compound C1=C2SC=CC2=CC(C2(O)CN(C)CC3=C2C=CC=C3OC)=C1 XYJGSJOLIMTUEJ-UHFFFAOYSA-N 0.000 description 1
- PTVBKFYPAAEHGV-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-8-methoxy-2-methyl-7-pyrazin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=CN=CC=N1 PTVBKFYPAAEHGV-UHFFFAOYSA-N 0.000 description 1
- PCCMYSOLZRFINM-UHFFFAOYSA-N 4-(1-benzothiophen-5-yl)-8-methoxy-2-methyl-7-pyrimidin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=CC=NC=N1 PCCMYSOLZRFINM-UHFFFAOYSA-N 0.000 description 1
- LNDGXNXQFYNWNA-UHFFFAOYSA-N 4-(2-chloro-1-benzothiophen-5-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=C(Cl)SC4=CC=3)C2=CC=C1C1=CC=CN=N1 LNDGXNXQFYNWNA-UHFFFAOYSA-N 0.000 description 1
- SFLGZLZAOGAMSA-UHFFFAOYSA-N 4-(2-chloro-1-benzothiophen-5-yl)-2-methyl-7-pyrimidin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2CN(C)CC(C=3C=C4C=C(Cl)SC4=CC=3)C2=CC=C1C1=NC=CC=N1 SFLGZLZAOGAMSA-UHFFFAOYSA-N 0.000 description 1
- MCMRJLWEQSVGJK-UHFFFAOYSA-N 4-(4-methoxy-1-benzothiophen-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-5-ol Chemical compound C1N(C)CC2=CC=CC(O)=C2C1C1=C(OC)C(C=CS2)=C2C=C1 MCMRJLWEQSVGJK-UHFFFAOYSA-N 0.000 description 1
- JRMIJYKTHQCXEO-UHFFFAOYSA-N 4-(4-methoxy-1-benzothiophen-5-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C1N(C)CC2=CC=CC=C2C1C1=C(OC)C(C=CS2)=C2C=C1 JRMIJYKTHQCXEO-UHFFFAOYSA-N 0.000 description 1
- ODRYIMKSTBYYFJ-UHFFFAOYSA-N 4-(4-methoxy-1-benzothiophen-5-yl)-2-methyl-7-pyrazin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=CC=2SC=CC=2C(OC)=C1C(C1=CC=2)CN(C)CC1=CC=2C1=CN=CC=N1 ODRYIMKSTBYYFJ-UHFFFAOYSA-N 0.000 description 1
- WOVXZSAOWZTTLL-UHFFFAOYSA-N 4-(4-methoxy-1-benzothiophen-5-yl)-2-methyl-7-pyridazin-3-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=CC=2SC=CC=2C(OC)=C1C(C1=CC=2)CN(C)CC1=CC=2C1=CC=CN=N1 WOVXZSAOWZTTLL-UHFFFAOYSA-N 0.000 description 1
- GUQVXYOQMQVGSX-UHFFFAOYSA-N 4-(4-methoxy-1-benzothiophen-5-yl)-2-methyl-7-pyrimidin-2-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=CC=2SC=CC=2C(OC)=C1C(C1=CC=2)CN(C)CC1=CC=2C1=NC=CC=N1 GUQVXYOQMQVGSX-UHFFFAOYSA-N 0.000 description 1
- WNZWBVBPMYEBRW-UHFFFAOYSA-N 4-(4-methoxy-1-benzothiophen-5-yl)-2-methyl-7-pyrimidin-4-yl-3,4-dihydro-1h-isoquinoline Chemical compound C1=CC=2SC=CC=2C(OC)=C1C(C1=CC=2)CN(C)CC1=CC=2C1=CC=NC=N1 WNZWBVBPMYEBRW-UHFFFAOYSA-N 0.000 description 1
- APNSMTUEKHRDEZ-UHFFFAOYSA-N 4-(6-fluoro-1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC2=CC=C(F)C=C2S1 APNSMTUEKHRDEZ-UHFFFAOYSA-N 0.000 description 1
- LPSBYWINFODMRX-UHFFFAOYSA-N 4-(7-chloro-1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC2=CC=CC(Cl)=C2S1 LPSBYWINFODMRX-UHFFFAOYSA-N 0.000 description 1
- BQQLZZIIYUWYPA-UHFFFAOYSA-N 4-[1-[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]cyclopropyl]morpholine Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1C1(N2CCOCC2)CC1 BQQLZZIIYUWYPA-UHFFFAOYSA-N 0.000 description 1
- XMYWLCXNKLAPKU-UHFFFAOYSA-N 4-[2-methyl-4-[3-(trifluoromethyl)-1-benzothiophen-5-yl]-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C(=CSC4=CC=3)C(F)(F)F)C2=CC=C1N1CCOCC1 XMYWLCXNKLAPKU-UHFFFAOYSA-N 0.000 description 1
- PGKQDDOQIQDXOR-UHFFFAOYSA-N 4-[4-(1-benzothiophen-2-yl)-2-ethyl-8-fluoro-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound FC1=C2CN(CC)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1N1CCOCC1 PGKQDDOQIQDXOR-UHFFFAOYSA-N 0.000 description 1
- KUZCTPOOLSLFGZ-UHFFFAOYSA-N 4-[4-(1-benzothiophen-2-yl)-5-fluoro-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=C(F)C=C1N1CCOCC1 KUZCTPOOLSLFGZ-UHFFFAOYSA-N 0.000 description 1
- JDOMAQYUWXLVMN-UHFFFAOYSA-N 4-[4-(1-benzothiophen-2-yl)-8-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound COC1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1N1CCOCC1 JDOMAQYUWXLVMN-UHFFFAOYSA-N 0.000 description 1
- FFVXTNKHQQBFKW-UHFFFAOYSA-N 4-[4-(2-chloro-1-benzothiophen-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3C=C4C=C(Cl)SC4=CC=3)C2=CC=C1N1CCOCC1 FFVXTNKHQQBFKW-UHFFFAOYSA-N 0.000 description 1
- OFBDURAPFGAEEB-UHFFFAOYSA-N 4-[4-(4-methoxy-1-benzothiophen-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=CC=2SC=CC=2C(OC)=C1C(C1=CC=2)CN(C)CC1=CC=2N1CCOCC1 OFBDURAPFGAEEB-UHFFFAOYSA-N 0.000 description 1
- JHWDUORRIPMRIT-UHFFFAOYSA-N 4-[4-(7-fluoro-1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3SC4=C(F)C=CC=C4C=3)C2=CC=C1N1CCOCC1 JHWDUORRIPMRIT-UHFFFAOYSA-N 0.000 description 1
- GOSWMXYLLTYURK-UHFFFAOYSA-N 4-[6-[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]pyridazin-3-yl]morpholine Chemical compound C1=C2CN(C)CC(C=3SC4=CC=CC=C4C=3)C2=CC=C1C(N=N1)=CC=C1N1CCOCC1 GOSWMXYLLTYURK-UHFFFAOYSA-N 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- HOJJQWZTVZBXTK-UHFFFAOYSA-N 5-(2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)-1-benzothiophen-4-ol Chemical compound C1=C2SC=CC2=C(O)C(C2CN(CC3=CC=CC=C32)C)=C1 HOJJQWZTVZBXTK-UHFFFAOYSA-N 0.000 description 1
- SAFDOQLZTRRBOO-UHFFFAOYSA-N 6-[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n,n-dimethylpyridazin-3-amine Chemical compound N1=NC(N(C)C)=CC=C1C1=CC=C(C(CN(C)C2)C=3SC4=CC=CC=C4C=3)C2=C1 SAFDOQLZTRRBOO-UHFFFAOYSA-N 0.000 description 1
- AKBJDQQVVDUYPH-UHFFFAOYSA-N 6-[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]-n-methylpyridazin-3-amine Chemical compound N1=NC(NC)=CC=C1C1=CC=C(C(CN(C)C2)C=3SC4=CC=CC=C4C=3)C2=C1 AKBJDQQVVDUYPH-UHFFFAOYSA-N 0.000 description 1
- CEXWADSTQWMWAX-UHFFFAOYSA-N 6-[4-(1-benzothiophen-2-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]quinazoline Chemical compound N1=CN=CC2=CC(C3=CC=C4C(C=5SC6=CC=CC=C6C=5)CN(CC4=C3)C)=CC=C21 CEXWADSTQWMWAX-UHFFFAOYSA-N 0.000 description 1
- MEIVAFGMGBGTNI-UHFFFAOYSA-N 6-[4-(1-benzothiophen-5-yl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl]pyridazin-3-amine Chemical compound C1=C2CN(C)CC(C=3C=C4C=CSC4=CC=3)C2=CC=C1C1=CC=C(N)N=N1 MEIVAFGMGBGTNI-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical class [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 102000014914 Carrier Proteins Human genes 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical class [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 206010013654 Drug abuse Diseases 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical group [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
- 101000835860 Homo sapiens SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily B member 1 Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical class CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- DUGOZIWVEXMGBE-UHFFFAOYSA-N Methylphenidate Chemical compound C=1C=CC=CC=1C(C(=O)OC)C1CCCCN1 DUGOZIWVEXMGBE-UHFFFAOYSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 101100187060 Mus musculus Nid1 gene Proteins 0.000 description 1
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 1
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- RTHCYVBBDHJXIQ-UHFFFAOYSA-N N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine Chemical compound C=1C=CC=CC=1C(CCNC)OC1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical class [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 102000008092 Norepinephrine Plasma Membrane Transport Proteins Human genes 0.000 description 1
- 108010049586 Norepinephrine Plasma Membrane Transport Proteins Proteins 0.000 description 1
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 206010033664 Panic attack Diseases 0.000 description 1
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 102100025746 SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily B member 1 Human genes 0.000 description 1
- 229940121991 Serotonin and norepinephrine reuptake inhibitor Drugs 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 206010066218 Stress Urinary Incontinence Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical class [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000012382 advanced drug delivery Methods 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 150000001298 alcohols Chemical group 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 239000002259 anti human immunodeficiency virus agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940124411 anti-hiv antiviral agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical class [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000003943 catecholamines Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
- 229960002023 chloroprocaine Drugs 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 229960001653 citalopram Drugs 0.000 description 1
- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000000599 controlled substance Substances 0.000 description 1
- 229940125368 controlled substance Drugs 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- JWOSTXBESVWMJW-UHFFFAOYSA-N cyclohexyl sulfamate Chemical class NS(=O)(=O)OC1CCCCC1 JWOSTXBESVWMJW-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000005046 dihydronaphthyl group Chemical group 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical class CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 229940052760 dopamine agonists Drugs 0.000 description 1
- 239000003136 dopamine receptor stimulating agent Substances 0.000 description 1
- 230000028436 dopamine uptake Effects 0.000 description 1
- 230000010249 dopaminergic function Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 230000002996 emotional effect Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical class CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical class OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- JUMYIBMBTDDLNG-OJERSXHUSA-N hydron;methyl (2r)-2-phenyl-2-[(2r)-piperidin-2-yl]acetate;chloride Chemical compound Cl.C([C@@H]1[C@H](C(=O)OC)C=2C=CC=CC=2)CCCN1 JUMYIBMBTDDLNG-OJERSXHUSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- LSYICPNAJSMBIC-UHFFFAOYSA-N hydroxymethyl hypofluorite Chemical group OCOF LSYICPNAJSMBIC-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical class OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 229960001344 methylphenidate Drugs 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 125000004370 n-butenyl group Chemical group [H]\C([H])=C(/[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005487 naphthalate group Chemical class 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 230000003982 neuronal uptake Effects 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000000966 norepinephrine reuptake Effects 0.000 description 1
- 229940127221 norepinephrine reuptake inhibitor Drugs 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OIPZNTLJVJGRCI-UHFFFAOYSA-M octadecanoyloxyaluminum;dihydrate Chemical compound O.O.CCCCCCCCCCCCCCCCCC(=O)O[Al] OIPZNTLJVJGRCI-UHFFFAOYSA-M 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical class CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 229940039748 oxalate Drugs 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229960002296 paroxetine Drugs 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229940035613 prozac Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- CBQGYUDMJHNJBX-RTBURBONSA-N reboxetine Chemical compound CCOC1=CC=CC=C1O[C@H](C=1C=CC=CC=1)[C@@H]1OCCNC1 CBQGYUDMJHNJBX-RTBURBONSA-N 0.000 description 1
- 229960003770 reboxetine Drugs 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229940099204 ritalin Drugs 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000003727 serotonin 1A antagonist Substances 0.000 description 1
- 239000003775 serotonin noradrenalin reuptake inhibitor Substances 0.000 description 1
- 230000000697 serotonin reuptake Effects 0.000 description 1
- 239000003772 serotonin uptake inhibitor Substances 0.000 description 1
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 1
- 229960002073 sertraline Drugs 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical class [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 210000000225 synapse Anatomy 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical class CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910001868 water Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4741—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having oxygen as a ring hetero atom, e.g. tubocuraran derivatives, noscapine, bicuculline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4743—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having sulfur as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/502—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with carbocyclic ring systems, e.g. cinnoline, phthalazine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/08—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with a hetero atom directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Reproductive Health (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Psychology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Gynecology & Obstetrics (AREA)
- Nutrition Science (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pregnancy & Childbirth (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58844804P | 2004-07-15 | 2004-07-15 | |
| PCT/US2005/025193 WO2006020049A2 (en) | 2004-07-15 | 2005-07-15 | Aryl-and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2007000428A true MX2007000428A (es) | 2008-03-05 |
Family
ID=35907927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2007000428A MX2007000428A (es) | 2004-07-15 | 2005-07-15 | Tetrahidroisoquinolinas sustituidas con arilo y heteroarilo y uso de las mismas para bloquear la captacion de norepinefrina, dopamina y serotonina. |
Country Status (17)
| Country | Link |
|---|---|
| US (7) | US7541357B2 (https=) |
| EP (1) | EP1778639B1 (https=) |
| JP (2) | JP5007226B2 (https=) |
| KR (2) | KR101389246B1 (https=) |
| CN (2) | CN103880827B (https=) |
| AU (1) | AU2005274927B2 (https=) |
| BR (1) | BRPI0513359A (https=) |
| CA (1) | CA2573271C (https=) |
| GE (1) | GEP20094640B (https=) |
| IL (1) | IL180349A (https=) |
| MX (1) | MX2007000428A (https=) |
| NO (1) | NO20070877L (https=) |
| NZ (1) | NZ552397A (https=) |
| RU (1) | RU2388751C2 (https=) |
| UA (1) | UA91341C2 (https=) |
| WO (1) | WO2006020049A2 (https=) |
| ZA (1) | ZA200701232B (https=) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA02004330A (es) * | 1999-11-03 | 2004-07-30 | Albany Molecular Res Inc | Tetrahidroisoquinolinas aril-y heteroaril-sustituidas y uso de las mismas para bloquear la recaptacion de norepinefrina, dopamina y serotonina.. |
| KR100821410B1 (ko) * | 2000-07-11 | 2008-04-10 | 에이엠알 테크놀로지, 인크. | 4-페닐 치환된 테트라하이드로이소퀴놀린 및 이의치료학적 용도 |
| NZ552397A (en) * | 2004-07-15 | 2011-04-29 | Amr Technology Inc | Aryl-and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| US20060111385A1 (en) * | 2004-11-22 | 2006-05-25 | Molino Bruce F | Novel 4-phenyl substituted tetrahydroisoquinolines and therapeutic use thereof |
| US20060111394A1 (en) * | 2004-11-22 | 2006-05-25 | Molino Bruce F | Aryl-and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine and serotonin |
| US20060111393A1 (en) * | 2004-11-22 | 2006-05-25 | Molino Bruce F | 4-Phenyl substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine and serotonin |
| KR20060059728A (ko) * | 2004-11-29 | 2006-06-02 | 삼성에스디아이 주식회사 | 액정 표시 장치 및 그 제조 방법 |
| KR101594898B1 (ko) | 2005-07-15 | 2016-02-18 | 알바니 몰레큘라 리써치, 인크. | 아릴- 및 헤테로아릴-치환된 테트라히드로벤자제핀, 및 노르에피네프린, 도파민 및 세로토닌의 재흡수를 차단하기 위한 용도 |
| WO2007095756A1 (en) * | 2006-02-27 | 2007-08-30 | Clera Inc. | Novel central-nervous system acting compounds and methods for the treatment of cns disorders |
| EP2727585A1 (en) | 2006-05-16 | 2014-05-07 | Takeda Pharmaceutical Company Limited | In-vivo screening method |
| EP2032558A1 (en) * | 2006-05-31 | 2009-03-11 | F. Hoffmann-Roche AG | Benzazepine derivatives as monoamine reuptake inhibitors |
| US20100010092A1 (en) * | 2006-12-19 | 2010-01-14 | Arless Ltd. | Use of modafinil to treat restless leg syndrome |
| EP2789338A3 (en) | 2007-11-15 | 2015-01-14 | Takeda Pharmaceutical Company Limited | Condensed pyridine derivate and use thereof |
| WO2009118765A2 (en) * | 2008-03-28 | 2009-10-01 | Panacea Biotec Limited | Novel monoamine re-uptake inhibitor |
| US9156812B2 (en) | 2008-06-04 | 2015-10-13 | Bristol-Myers Squibb Company | Crystalline form of 6-[(4S)-2-methyl-4-(2-naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine |
| AR071997A1 (es) * | 2008-06-04 | 2010-07-28 | Bristol Myers Squibb Co | Forma cristalina de 6-((4s)-2-metil-4-(2-naftil)-1,2,3,4-tetrahidroisoquinolin-7-il)piridazin-3-amina |
| AR072297A1 (es) | 2008-06-27 | 2010-08-18 | Novartis Ag | Derivados de indol-2-il-piridin-3-ilo, composicion farmaceutica que los comprende y su uso en medicamentos para el tratamiento de enfermedades mediadas por la sintasa aldosterona. |
| US8193363B2 (en) * | 2008-08-29 | 2012-06-05 | Astrazeneca Ab | Compounds suitable as precursors to compounds that are useful for imaging amyloid deposits |
| WO2010080503A1 (en) * | 2008-12-19 | 2010-07-15 | Genentech, Inc. | Heterocyclic compounds and methods of use |
| RU2402534C1 (ru) * | 2009-04-27 | 2010-10-27 | Государственное образовательное учреждение высшего профессионального образования "Пермский государственный университет" | (1z,3z)-4-гидрокси-1-(3-бутил-3-метил-3,4-дигидроизохинолин-1(2н)-илиден)-4-(4-толил)бут-3-ен-2-он, проявляющий анальгетическую и противовоспалительную активность |
| AU2010247763B2 (en) | 2009-05-12 | 2015-12-24 | Albany Molecular Research, Inc. | 7-([1,2,4,]triazolo[1,5,-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4- tetrahydroisoquinoline and use thereof |
| AU2010247735B2 (en) * | 2009-05-12 | 2015-07-16 | Albany Molecular Research, Inc. | Crystalline forms of (S)-7-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)- 1,2,3,4-tetrahydroisoquinoline and use thereof |
| WO2010132437A1 (en) * | 2009-05-12 | 2010-11-18 | Albany Molecular Research, Inc. | Aryl, heteroaryl, and heterocycle substituted tetrahydroisoquinolines and use thereof |
| JP5763313B2 (ja) * | 2009-09-03 | 2015-08-12 | 富山化学工業株式会社 | 2−(1−ベンゾチオフェン−5−イル)エタノールの製造法 |
| WO2012024397A2 (en) | 2010-08-17 | 2012-02-23 | Albany Molecular Research, Inc. | 2,5-methano-and 2,5-ethano-tetrahydrobenzazepine derivatives and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| US9073881B2 (en) | 2011-09-23 | 2015-07-07 | Hoffmann-La Roche Inc. | Benzoic acid derivatives |
| US8969586B2 (en) | 2011-09-27 | 2015-03-03 | Bristol-Myers Squibb Company | Substituted bicyclic heteroaryl compounds |
| TWI561521B (en) * | 2011-10-14 | 2016-12-11 | Abbvie Inc | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
| CA2886117C (en) * | 2012-10-05 | 2022-05-31 | Merck Sharp & Dohme Corp. | Indoline compounds and their use as aldosterone synthase inhibitors |
| WO2014159501A2 (en) * | 2013-03-14 | 2014-10-02 | Bristol-Myers Squibb Company | Processes for preparing tetrahydroisoquinolines |
| CN104402816A (zh) * | 2014-10-28 | 2015-03-11 | 常州大学 | 一种苯并吡啶甲酸的合成方法 |
| CA3011201C (en) * | 2016-01-15 | 2020-09-22 | Pfizer Inc. | 6,7,8,9-tetrahydro-5h-pyrido[2,3-d]azepine dopamine d3 ligands |
| CN108884050B (zh) * | 2016-04-13 | 2022-07-05 | Ucb生物制药私人有限公司 | 四氢异喹啉衍生物 |
| US20190218214A1 (en) * | 2016-09-14 | 2019-07-18 | Vanderbilt University | Inhibition of BMP Signaling Compounds, Compositions and Uses Thereof |
| WO2018065288A1 (de) | 2016-10-07 | 2018-04-12 | Bayer Cropscience Aktiengesellschaft | 2-[2-phenyl-1-(sulfonylmethyl)vinyl]-imidazo[4,5-b]pyridin-derivate und verwandte verbindungen als schädlingsbekämpfungsmittel im pflanzenschutz |
| AR113206A1 (es) | 2017-01-10 | 2020-02-19 | Bayer Cropscience Ag | Derivados heterocíclicos como pesticidas |
| UY37556A (es) | 2017-01-10 | 2018-07-31 | Bayer Ag | Derivados heterocíclicos como pesticidas |
| CN107141202A (zh) * | 2017-06-29 | 2017-09-08 | 白银龙铭化工科技有限公司 | 7‑溴‑3,4‑二氢‑1(2h)‑萘酮化合物的合成方法 |
| US20210052600A1 (en) | 2017-12-27 | 2021-02-25 | Takeda Pharmaceutical Company Limited | Therapeutic agents for stress urinary incontinence and incotinence of feces |
| EP3737677B1 (en) * | 2018-01-10 | 2021-11-03 | Allinky Biopharma | Tetrahydroisoquinoline compounds |
| CN113195084B (zh) * | 2018-10-10 | 2024-04-09 | 阿尔伯爱因斯坦医学院 | 可用作分子伴侣介导的自噬调节剂的苯并噁唑及相关化合物 |
| CN109400453B (zh) * | 2018-12-13 | 2021-04-27 | 河南师范大学 | 一种2,6-二溴苯甲醛的制备方法 |
| CN117447376A (zh) * | 2019-12-09 | 2024-01-26 | 苏州恩华生物医药科技有限公司 | 连双环结构sigma-1受体抑制剂 |
| CN114702478B (zh) * | 2020-12-18 | 2024-01-05 | 上海济煜医药科技有限公司 | 苯并杂环取代四氢异喹啉类化合物 |
| CN114315796B (zh) * | 2021-12-30 | 2024-03-26 | 中国药科大学 | 用作hpk1激酶抑制剂的化合物及其制备方法和应用 |
Family Cites Families (305)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH527194A (de) | 1970-01-06 | 1972-08-31 | Hoffmann La Roche | Verfahren zur Herstellung von Isochinolin-Derivaten |
| US3666763A (en) | 1970-01-06 | 1972-05-30 | Hoffmann La Roche | 4-phenyl isoquinolines and process for preparing same |
| US3947456A (en) * | 1970-01-06 | 1976-03-30 | Hoffman-La Roche Inc. | Substituted 4-phenyl isoquinolines |
| JPS5223083B2 (https=) | 1972-03-31 | 1977-06-22 | ||
| JPS5223083Y2 (https=) | 1972-06-23 | 1977-05-26 | ||
| GB1504424A (en) * | 1975-08-09 | 1978-03-22 | Beecham Group Ltd | Isoquinoline-derived aminoethers |
| US4340600A (en) * | 1980-05-22 | 1982-07-20 | Smithkline Corporation | Renal dilating methods and compositions using 4-(3,4-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinolines |
| DE3333994A1 (de) * | 1983-09-21 | 1985-04-04 | Troponwerke GmbH & Co KG, 5000 Köln | Neue pyridoindolderivate, verfahren zu ihrer herstellung und ihre verwendung |
| US4843071A (en) | 1986-12-05 | 1989-06-27 | Serotonin Industries Of Charleston | Method and composition for treating obesity, drug abuse, and narcolepsy |
| CA1327795C (en) | 1987-08-14 | 1994-03-15 | Jules Freedman | Antidepressants which are aryloxy inadanamines |
| EP0360390A1 (en) | 1988-07-25 | 1990-03-28 | Glaxo Group Limited | Spirolactam derivatives |
| MX18467A (es) | 1988-11-23 | 1993-07-01 | Pfizer | Agentes terapeuticos de quinuclidinas |
| FI895821A7 (fi) | 1988-12-07 | 1990-06-08 | The Wellcome Foundation Ltd | Farmaseuttisesti aktivisia CNS-yhdisteitä |
| US4902710A (en) * | 1988-12-14 | 1990-02-20 | Eli Lilly And Company | Serotonin and norepinephrine uptake inhibitors |
| US5114976A (en) * | 1989-01-06 | 1992-05-19 | Norden Michael J | Method for treating certain psychiatric disorders and certain psychiatric symptoms |
| EP0380223A1 (en) | 1989-01-17 | 1990-08-01 | Konica Corporation | Colour filter and process for producing the same |
| JPH02281203A (ja) | 1989-04-21 | 1990-11-16 | Konica Corp | カラーフィルター |
| BG49761A1 (en) | 1989-04-24 | 1992-02-14 | Vissh Khim T I | 4- (4'- chalophenyl)- 2- methyl- 1, 2, 3, 4- tetrahydroisohinolines and method for its preparation |
| US5164372A (en) | 1989-04-28 | 1992-11-17 | Fujisawa Pharmaceutical Company, Ltd. | Peptide compounds having substance p antagonism, processes for preparation thereof and pharmaceutical composition comprising the same |
| AU6368090A (en) | 1989-10-03 | 1991-04-11 | Warner-Lambert Company | Substituted carboxytetrahydroisoquinolines and derivatives thereof having pharmaceutical activity |
| FI97540C (fi) | 1989-11-06 | 1997-01-10 | Sanofi Sa | Menetelmä terapeuttisesti käyttökelpoisten, aromaattisesti substituoitujen piperidiini- ja piperatsiinijohdannaisten valmistamiseksi |
| FR2654726B1 (fr) | 1989-11-23 | 1992-02-14 | Rhone Poulenc Sante | Nouveaux derives de l'isoindolone et leur preparation. |
| FR2654725B1 (fr) | 1989-11-23 | 1992-02-14 | Rhone Poulenc Sante | Nouveaux derives de l'isoindolone, leur preparation et les compositions pharmaceutiques qui les contiennent. |
| GB8929070D0 (en) | 1989-12-22 | 1990-02-28 | Fujisawa Pharmaceutical Co | Peptide compounds,processes for preparation thereof and pharmaceutical composition comprising the same |
| US5232929A (en) | 1990-11-28 | 1993-08-03 | Pfizer Inc. | 3-aminopiperidine derivatives and related nitrogen containing heterocycles and pharmaceutical compositions and use |
| UA41251C2 (uk) | 1990-01-04 | 2001-09-17 | Пфайзер, Інк. | Гідровані азотвмісні гетероциклічні сполуки, похідні піперидину, фармацевтична композиція та спосіб пригнічення активності речовини р в організмі |
| US5321032A (en) | 1990-02-15 | 1994-06-14 | Fujisawa Pharmaceutical Co., Ltd. | Peptide compounds and pharmaceutical compositions thereof |
| US5447947A (en) | 1990-02-26 | 1995-09-05 | Arc 1 | Compositions and methods of treatment of sympathetically maintained pain |
| JPH072740B2 (ja) | 1990-06-01 | 1995-01-18 | フアイザー・インコーポレイテツド | 3―アミノ―2―アリールキヌクリジン |
| ATE116317T1 (de) | 1990-07-23 | 1995-01-15 | Pfizer | Chinuclidinderivate. |
| AU687754B2 (en) | 1990-08-31 | 1998-03-05 | Warner-Lambert Company | Tachykinin antagonists |
| HUT68667A (en) | 1990-09-28 | 1995-07-28 | Pfizer | Fused ring analogs of nitrogen containing nonaromatic heterocycles |
| GB9023116D0 (en) | 1990-10-24 | 1990-12-05 | Fujisawa Pharmaceutical Co | Peptide compounds,processes for preparation thereof and pharmaceutical composition comprising the same |
| JPH04193867A (ja) | 1990-11-23 | 1992-07-13 | Nippon Shinyaku Co Ltd | イソキノリノール誘導体及び医薬 |
| DK0498069T3 (da) | 1990-12-21 | 1995-12-04 | Fujisawa Pharmaceutical Co | Ny anvendelse af peptidderivat |
| EP0566589A1 (en) | 1991-01-10 | 1993-10-27 | Pfizer Inc. | N-alkyl quinuclidinium salts as substance p antagonists |
| EP0499313B1 (en) | 1991-02-11 | 1997-06-11 | MERCK SHARP & DOHME LTD. | Azabicyclic compounds, pharmaceutical compositions containing them and their use in therapy |
| ES2065175T3 (es) | 1991-03-01 | 1995-02-01 | Pfizer | Derivados de 1-azabiciclo(3.2.2)nonan-3-amina. |
| SK284565B6 (sk) | 1991-03-26 | 2005-06-02 | Pfizer Inc. | Spôsob prípravy substituovaných piperidínov |
| FR2677361A1 (fr) | 1991-06-04 | 1992-12-11 | Adir | Nouveaux peptides et pseudopeptides, derives de tachykinines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2676053B1 (fr) | 1991-05-03 | 1993-08-27 | Sanofi Elf | Nouveaux composes dialkylenepiperidino et leurs enantiomeres, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| FR2676055B1 (fr) | 1991-05-03 | 1993-09-03 | Sanofi Elf | Composes polycycliques amines et leurs enantiomeres, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| FR2676443B1 (fr) | 1991-05-17 | 1993-08-06 | Rhone Poulenc Rorer Sa | Nouveaux derives de perhydroisoindole et leur preparation. |
| FR2676446B1 (fr) | 1991-05-17 | 1993-08-06 | Rhone Poulenc Rorer Sa | Nouveaux derives du thiopyranopyrrole, leur preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2676447B1 (fr) | 1991-05-17 | 1993-08-06 | Rhone Poulenc Rorer Sa | Nouveaux derives du thiopyranopyrrole et leur preparation. |
| FR2676442B1 (fr) | 1991-05-17 | 1993-08-06 | Rhone Poulenc Rorer Sa | Nouveau derives de perhydroisoindole, leur preparation et les compositions pharmaceutiques qui les contiennent. |
| PL171921B1 (pl) | 1991-05-22 | 1997-06-30 | Pfizer | Sposób wytwarzania nowych pochodnych podstawionej 3-aminochinuklidyny PL PL PL PL PL |
| WO1992020661A1 (en) | 1991-05-22 | 1992-11-26 | Merck & Co., Inc. | N, n-diacylpiperazines |
| UA27776C2 (uk) | 1991-05-31 | 2000-10-16 | Пфайзер Інк. | Похідні хінуклідину та їх фармацевтично прийнятні солі, що є антагоністами речовини р у ссавців, фармацевтична композиція, що має антагоністичну дію на речовину р у ссавців |
| GB9113219D0 (en) | 1991-06-19 | 1991-08-07 | Fujisawa Pharmaceutical Co | Peptide compound,processes for preparation thereof and pharmaceutical composition comprising the same |
| FI990419A7 (fi) | 1991-06-20 | 1999-02-26 | Pfizer | Typpeä sisältävien hetrosyklisten yhdisteiden fluorialkoksibentsyyliaminojohdannaiset |
| TW202432B (https=) | 1991-06-21 | 1993-03-21 | Pfizer | |
| US5288730A (en) | 1991-06-24 | 1994-02-22 | Merck Sharp & Dohme Limited | Azabicyclic compounds, pharmaceutical compositions containing them and their use in therapy |
| JPH06509332A (ja) | 1991-07-05 | 1994-10-20 | メルク シヤープ エンド ドーム リミテツド | 芳香族化合物、それらを含む医薬組成物、及び治療におけるそれらの使用 |
| EP0536817A1 (en) | 1991-07-05 | 1993-04-14 | MERCK SHARP & DOHME LTD. | Azabicyclic compounds as tachykinin antagonists |
| US5472978A (en) | 1991-07-05 | 1995-12-05 | Merck Sharp & Dohme Ltd. | Aromatic compounds, pharmaceutical compositions containing them and their use in therapy |
| WO1993001165A2 (en) | 1991-07-10 | 1993-01-21 | Merck Sharp & Dohme Limited | Aromatic compounds, compositions containing them and their use in therapy |
| US5495047A (en) | 1991-07-10 | 1996-02-27 | Merck, Sharp & Dohme (Ltd.) | Fused tricyclic compounds, pharmaceutical compositions containing them and their use in therapy |
| MY110227A (en) | 1991-08-12 | 1998-03-31 | Ciba Geigy Ag | 1-acylpiperindine compounds. |
| EP0600952B1 (en) | 1991-08-20 | 1996-04-17 | MERCK SHARP & DOHME LTD. | Azacyclic compounds, processes for their preparation and pharmaceutical compositions containing them |
| DE69231395T3 (de) | 1991-09-20 | 2005-07-21 | Glaxo Group Ltd., Greenford | Neue medizinische Indikation für Tachykinin-Antagonisten |
| CZ59394A3 (en) | 1991-09-26 | 1994-11-16 | Pfizer | Condensed tricyclic heterocycles containing nitrogen as antagonists of p substance receptor, process of their preparation, intermediates, pharmaceutical preparations in which they are comprised and use |
| JP2553020B2 (ja) | 1991-11-07 | 1996-11-13 | 吉富製薬株式会社 | キヌクリジン化合物およびその医薬用途 |
| DK0613458T3 (da) | 1991-11-12 | 1998-02-09 | Pfizer | Acykliske ethylendiaminderivater som substans P receptorantagonister |
| CA2083891A1 (en) | 1991-12-03 | 1993-06-04 | Angus Murray Macleod | Heterocyclic compounds, compositions containing them and their use in therapy |
| GB9200535D0 (en) | 1992-01-10 | 1992-02-26 | Fujisawa Pharmaceutical Co | New compound |
| GB9201179D0 (en) | 1992-01-21 | 1992-03-11 | Glaxo Group Ltd | Chemical compounds |
| US5241065A (en) | 1992-02-25 | 1993-08-31 | Schering Corporation | 2,3,4,5-tetrahydro-1h-3-benzazepines having anti-psychotic activity |
| US5328927A (en) | 1992-03-03 | 1994-07-12 | Merck Sharpe & Dohme, Ltd. | Hetercyclic compounds, processes for their preparation and pharmaceutical compositions containing them |
| US5595872A (en) | 1992-03-06 | 1997-01-21 | Bristol-Myers Squibb Company | Nucleic acids encoding microsomal trigyceride transfer protein |
| JP2656702B2 (ja) | 1992-03-23 | 1997-09-24 | ファイザー製薬株式会社 | ペプチド性キヌクリジン |
| FR2689888B1 (fr) | 1992-04-10 | 1994-06-10 | Rhone Poulenc Rorer Sa | Nouveaux derives de perhydroisoindole, leur preparation et les compositions pharmaceutiques qui les contiennent. |
| EP0636130A1 (en) | 1992-04-15 | 1995-02-01 | Merck Sharp & Dohme Ltd. | Azacyclic compounds |
| GB2266529A (en) | 1992-05-01 | 1993-11-03 | Merck Sharp & Dohme | Tetrahydroisoquinoline derivatives |
| EP0641328B1 (en) | 1992-05-18 | 2001-11-21 | Pfizer Inc. | Bridged aza-bicyclic derivatives as substance p antagonists |
| GB9211193D0 (en) | 1992-05-27 | 1992-07-08 | Merck Sharp & Dohme | Therapeutic agents |
| IL106142A (en) | 1992-06-29 | 1997-03-18 | Merck & Co Inc | Morpholine and thiomorpholine tachykinin receptor antagonists, their preparation and pharmaceutical compositions containing them |
| WO1994001402A1 (en) | 1992-07-13 | 1994-01-20 | Merck Sharp & Dohme Limited | Heterocyclic amide derivatives as tachykinin derivatives |
| EP0786522A2 (en) | 1992-07-17 | 1997-07-30 | Ribozyme Pharmaceuticals, Inc. | Enzymatic RNA molecules for treatment of stenotic conditions |
| GB2268931A (en) | 1992-07-22 | 1994-01-26 | Merck Sharp & Dohme | Azabicyclic tachykinin-receptor antagonists |
| ES2124318T3 (es) | 1992-07-28 | 1999-02-01 | Merck Sharp & Dohme | Compuestos azaciclicos. |
| GB2269170A (en) | 1992-07-29 | 1994-02-02 | Merck Sharp & Dohme | Azatricyclic tachykinin antagonists |
| AU4718093A (en) | 1992-07-31 | 1994-03-03 | Merck Sharp & Dohme Limited | Substituted amines as tachykinin receptor antagonists |
| AU4396193A (en) | 1992-08-04 | 1994-03-03 | Pfizer Inc. | 3-benzylamino-2-phenyl-piperidine derivatives as substance p receptor antagonists |
| GB9216911D0 (en) | 1992-08-10 | 1992-09-23 | Merck Sharp & Dohme | Therapeutic agents |
| US5212185A (en) | 1992-08-14 | 1993-05-18 | G. D. Searle & Co. | Piperidinyl-terminated alkylamino ethynyl alanine amino diol compounds for treatment of hypertension |
| ATE208376T1 (de) | 1992-08-19 | 2001-11-15 | Pfizer | Substituierte benzylamin-stickstoff enthaltende nichtaromatische heterocyclen |
| EP0585913B1 (en) | 1992-09-04 | 1997-12-29 | Takeda Chemical Industries, Ltd. | Condensed heterocyclic compounds, their production and use |
| AU4973693A (en) | 1992-09-10 | 1994-03-29 | Merck Sharp & Dohme Limited | Alcohols and ethers with aromatic substituents as tachykinin-antagonists |
| GB9220286D0 (en) | 1992-09-25 | 1992-11-11 | Merck Sharp & Dohme | Therapeutic agents |
| GB2271566A (en) | 1992-10-14 | 1994-04-20 | Merck & Co Inc | HIV integrase inhibitors |
| JP2656699B2 (ja) | 1992-10-21 | 1997-09-24 | ファイザー製薬株式会社 | 置換ベンジルアミノキヌクリジン |
| GB9222262D0 (en) | 1992-10-23 | 1992-12-09 | Merck Sharp & Dohme | Therapeutic agents |
| GB9222486D0 (en) | 1992-10-26 | 1992-12-09 | Merck Sharp & Dohme | Therapeutic agents |
| AU678409B2 (en) | 1992-10-28 | 1997-05-29 | Merck Sharp & Dohme Limited | 4-arylmethyloxymethyl piperidines as tachykinin antagonists |
| JP2656700B2 (ja) | 1992-10-28 | 1997-09-24 | ファイザー製薬株式会社 | 置換キヌクリジン誘導体 |
| WO1994010167A1 (en) | 1992-10-30 | 1994-05-11 | Merck Sharp & Dohme Limited | Tachykinin antagonists |
| DK0668863T3 (da) | 1992-11-12 | 1997-06-30 | Pfizer | Quinuclidinderivat som substans P-antagonist |
| US5261188A (en) | 1992-11-23 | 1993-11-16 | The Standard Products Company | Belt weatherstrip with bulb |
| JPH06153997A (ja) | 1992-11-27 | 1994-06-03 | Canon Inc | 検出信号増幅による標的核酸の検出方法 |
| CA2150123C (en) | 1992-12-10 | 2004-12-07 | Harry R. Howard | Aminomethylene substituted non-aromatic heterocycles |
| US5661162A (en) | 1992-12-14 | 1997-08-26 | Merck Sharp & Dohme Limited | 4-aminomethyl/thiomethyl/sulfonylmethyl-4-phenylpiperdines as tachykinin receptor antagonists |
| GB9226581D0 (en) | 1992-12-21 | 1993-02-17 | Merck Sharp & Dohme | Therapeutic agents |
| DK154192D0 (da) * | 1992-12-23 | 1992-12-23 | Neurosearch As | Heterocycliske forbindelser |
| GB9300051D0 (en) | 1993-01-04 | 1993-03-03 | Merck Sharp & Dohme | Therapeutic agents |
| US5466689A (en) | 1993-02-08 | 1995-11-14 | Takeda Chemical Industries, Ltd. | Morpholine derivatives and their use |
| ATE166867T1 (de) | 1993-02-18 | 1998-06-15 | Merck Sharp & Dohme | Azacyclische verbindungen, sie enthaltende zusammensetzungen und ihre verwendung als tachykinin antagoniste |
| US5674889A (en) | 1993-02-22 | 1997-10-07 | Merck, Sharp & Dohme, Ltd. | Aromatic compounds, compositions containing them and their use in therapy |
| DE69318854T2 (de) | 1993-03-04 | 1998-10-08 | Pfizer | Spiroazacyclischderivate als substanz p antagonisten |
| US5656642A (en) | 1993-04-07 | 1997-08-12 | Otsuka Pharmaceutical Co., Ltd. | Peripheral vasodilating agent containing piperidine derivative as active ingredient |
| WO1994026735A1 (en) | 1993-05-06 | 1994-11-24 | Merrell Dow Pharmaceuticals Inc. | Substituted pyrrolidin-3-yl-alkyl-piperidines useful as tachykinin antagonists |
| IL109646A0 (en) | 1993-05-19 | 1994-08-26 | Pfizer | Heteroatom substituted alkyl benzylamino-quinuclidines |
| JPH08511522A (ja) | 1993-06-07 | 1996-12-03 | メルク エンド カンパニー インコーポレーテッド | ニューロキニンアンタゴニストとしてのスピロ置換アザ環 |
| EP0634402A1 (en) | 1993-07-14 | 1995-01-18 | Takeda Chemical Industries, Ltd. | Isochinolinone derivatives, their production and use |
| WO1995002595A1 (en) | 1993-07-15 | 1995-01-26 | Pfizer Inc. | Benzyloxyquinuclidines as substance p antagonists |
| GB9315808D0 (en) | 1993-07-30 | 1993-09-15 | Merck Sharp & Dohme | Therapeutic agents |
| TW365603B (en) | 1993-07-30 | 1999-08-01 | Rhone Poulenc Rorer Sa | Novel perhydroisoindole derivatives, their preparation and pharmaceutical compositions which contain them |
| GB9317987D0 (en) | 1993-08-26 | 1993-10-13 | Glaxo Group Ltd | Chemical compounds |
| AU7082194A (en) | 1993-09-17 | 1995-04-03 | Pfizer Inc. | Heteroarylamino and heteroarylsulfonamido substituted 3-benzylaminomethyl piperidines and related compounds |
| WO1995007886A1 (en) | 1993-09-17 | 1995-03-23 | Pfizer Inc. | 3-amino-5-carboxy-substituted piperidines and 3-amino-4-carboxy-substituted pyrrolidines as tachykinin antagonists |
| IS4208A (is) | 1993-09-22 | 1995-03-23 | Glaxo Group Limited | 3-(tetrazólýl-benzyl)amínó-piperadidín afleiður |
| WO1995011880A1 (en) | 1993-10-27 | 1995-05-04 | Merck Sharp & Dohme Limited | Substituted amides as tachykinin antagonists |
| US6403577B1 (en) | 1993-11-17 | 2002-06-11 | Eli Lilly And Company | Hexamethyleneiminyl tachykinin receptor antagonists |
| IT1271462B (it) | 1993-12-03 | 1997-05-28 | Menarini Farma Ind | Antagonisti delle tachichinine,procedimento per la loro preparazione e loro impiego in formulazioni farmaceutiche. |
| IL111960A (en) | 1993-12-17 | 1999-12-22 | Merck & Co Inc | Morpholines and thiomorpholines their preparation and pharmaceutical compositions containing them |
| WO1995017382A1 (en) | 1993-12-21 | 1995-06-29 | Eli Lilly And Company | Non-peptide tachykinin receptor antagonists |
| HUT74682A (en) | 1993-12-29 | 1997-01-28 | Pfizer | Diazabicyclic neurokinin antagonists and pharmaceutical compositions containing them |
| IL112134A (en) | 1993-12-29 | 1999-12-22 | Merck Sharp & Dohme | Substituted morpholine derivatives their preparation and pharmaceutical compositions containing them |
| JPH09508376A (ja) | 1994-01-28 | 1997-08-26 | メルク シヤープ エンド ドーム リミテツド | アラルキル置換アザシクロ系の治療薬 |
| GB9402688D0 (en) | 1994-02-11 | 1994-04-06 | Merck Sharp & Dohme | Therapeutic agents |
| US5610165A (en) | 1994-02-17 | 1997-03-11 | Merck & Co., Inc. | N-acylpiperidine tachykinin antagonists |
| IL112778A0 (en) | 1994-03-04 | 1995-05-26 | Merck & Co Inc | Substituted heterocycles, their preparation and pharmaceutical compositions containing them |
| FR2718136B1 (fr) | 1994-03-29 | 1996-06-21 | Sanofi Sa | Composés aromatiques aminés, procédé pour leur obtention et compositions pharmaceutiques les contenant. |
| US5610145A (en) | 1994-04-15 | 1997-03-11 | Warner-Lambert Company | Tachykinin antagonists |
| US5607939A (en) * | 1994-04-28 | 1997-03-04 | Takeda Chemical Industries, Ltd. | Condensed heterocyclic compounds, their production and use |
| PE27997A1 (es) | 1994-04-29 | 1997-09-20 | Lilly Co Eli | Antagonistas de receptores de taquicininas |
| WO1995030674A1 (en) | 1994-05-05 | 1995-11-16 | Merck Sharp & Dohme Limited | Morpholine derivatives and their use as antagonists of tachikinins |
| AU690275B2 (en) | 1994-05-07 | 1998-04-23 | Boehringer Ingelheim International Gmbh | Neurokinine (tachykinine) antagonists |
| ES2165915T3 (es) | 1994-06-06 | 2002-04-01 | Warner Lambert Co | Antagonistas del receptor de la taquiquinina (nk 1). |
| EP0686629A3 (en) | 1994-06-10 | 1999-02-10 | Eli Lilly And Company | Cyclohexyl tachykinine receptor antagonists |
| CA2134038C (en) | 1994-06-16 | 1997-06-03 | David Taiwai Wong | Potentiation of drug response |
| WO1996001819A1 (en) | 1994-07-12 | 1996-01-25 | Eli Lilly And Company | Heterocyclic tachykinin receptor antagonists |
| CN1157610A (zh) | 1994-07-20 | 1997-08-20 | 比克·古尔顿·劳姆贝尔格化学公司 | 抗螺杆菌的吡啶基硫基化合物 |
| DE4425612A1 (de) | 1994-07-20 | 1996-04-04 | Bayer Ag | 6-gliedrige stickstoffhaltige Heteroaryl-oxazolidinone |
| CA2154116A1 (en) | 1994-07-22 | 1996-01-23 | Philip Arthur Hipskind | 1-aryl-2-acetamidopentanone derivatives for use as tachykinin receptor antagonists |
| GB9415996D0 (en) | 1994-08-08 | 1994-09-28 | Merck Sharp & Dohme | Therapeutic agents |
| GB9415997D0 (en) | 1994-08-08 | 1994-09-28 | Merck Sharp & Dohme | Therapeutic agents |
| TW432061B (en) | 1994-08-09 | 2001-05-01 | Pfizer Res & Dev | Lactams |
| US5824678A (en) | 1994-08-15 | 1998-10-20 | Merck Sharp & Dohme Ltd. | Morpholine derivatives and their use as therapeutic agents |
| CA2198084C (en) | 1994-08-25 | 2000-03-28 | Timothy P. Burkholder | Novel substituted piperidines useful for the treatment of allergic diseases |
| DE69405864T2 (de) | 1994-08-29 | 1998-03-26 | Akzo Nobel Nv | Verfahren zur Herstellung von quaternären Diestern |
| GB9417956D0 (en) | 1994-09-02 | 1994-10-26 | Merck Sharp & Dohme | Therapeutic agents |
| GB9418545D0 (en) | 1994-09-15 | 1994-11-02 | Merck Sharp & Dohme | Therapeutic agents |
| US5457107A (en) | 1994-09-16 | 1995-10-10 | Merck & Co., Inc. | Polymorphic form of a tachykinin receptor antagonist |
| HUT77318A (hu) | 1994-09-30 | 1998-03-30 | Novartis Ag. | 1-Acil-4-/(alifás amino)-piperidin/-származékok, e vegyületeket tartalmazó gyógyszerkészítmények, eljárás előállításukra és alkalmazásuk |
| TW397825B (en) | 1994-10-14 | 2000-07-11 | Novartis Ag | Aroyl-piperidine derivatives |
| FR2725986B1 (fr) | 1994-10-21 | 1996-11-29 | Adir | Nouveaux derives de piperidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| DE69534213T2 (de) | 1994-10-25 | 2006-01-12 | Astrazeneca Ab | Therapeutisch wirksame Heterocyclen |
| GB9421709D0 (en) | 1994-10-27 | 1994-12-14 | Zeneca Ltd | Therapeutic compounds |
| EP0714891A1 (en) | 1994-11-22 | 1996-06-05 | Eli Lilly And Company | Heterocyclic tachykinin receptor antagonists |
| FR2727411B1 (fr) | 1994-11-30 | 1997-01-03 | Rhone Poulenc Rorer Sa | Nouveaux derives de perhydroisoindole, leur preparation et les compositions pharmaceutiques qui les contiennent |
| PE38997A1 (es) | 1994-12-13 | 1997-10-02 | Novartis Ag | Antagonista de taquicinina |
| GB9426103D0 (en) | 1994-12-23 | 1995-02-22 | Merck Sharp & Dohme | Therapeutic agents |
| EP0802912B1 (en) | 1995-01-12 | 2004-10-13 | Glaxo Group Limited | Piperidine derivatives having tachykinin antagonist activity |
| FR2729951B1 (fr) | 1995-01-30 | 1997-04-18 | Sanofi Sa | Nouveaux composes heterocycliques, procede pour leur preparation et compositions pharmaceutiques en contenant |
| GB9505491D0 (en) | 1995-03-18 | 1995-05-03 | Merck Sharp & Dohme | Therapeutic agents |
| GB9505492D0 (en) | 1995-03-18 | 1995-05-03 | Merck Sharp & Dohme | Therapeutic agents |
| US5554641A (en) | 1995-03-20 | 1996-09-10 | Horwell; David C. | Nonpeptides as tachykinin antagonists |
| GB9505692D0 (en) | 1995-03-21 | 1995-05-10 | Glaxo Group Ltd | Chemical compounds |
| EP0733632B1 (en) | 1995-03-24 | 2003-06-04 | Takeda Chemical Industries, Ltd. | Cyclic compounds, their production and use as tachykinin receptor antagonists |
| US5565568A (en) | 1995-04-06 | 1996-10-15 | Eli Lilly And Company | 2-acylaminopropanamides as tachykinin receptor antagonists |
| JP3950170B2 (ja) | 1995-04-13 | 2007-07-25 | アベンティス・ファーマスーティカルズ・インコーポレイテッド | タキキニン受容体アンタゴニスト活性を有する新規な置換されたピペラジン誘導体 |
| NZ307625A (en) | 1995-05-25 | 1999-02-25 | Fujisawa Pharmaceutical Co | 1-benzoyl-2-(indolyl-3-alkyl)-piperazine derivatives as neurokinin receptor antagonists |
| US5654316A (en) | 1995-06-06 | 1997-08-05 | Schering Corporation | Piperidine derivatives as neurokinin antagonists |
| US5817832A (en) | 1995-06-22 | 1998-10-06 | Ciba Specialty Chemicals Corporation | Blue diketopyrrolopyrrole pigments |
| GB9513121D0 (en) | 1995-06-28 | 1995-08-30 | Merck Sharp & Dohme | Therapeutic agents |
| GB9513117D0 (en) | 1995-06-28 | 1995-08-30 | Merck Sharp & Dohme | Therapeutic agents |
| GB9513118D0 (en) | 1995-06-28 | 1995-08-30 | Merck Sharp & Dohme | Therapeutic agents |
| MX9800187A (es) | 1995-07-07 | 1998-05-31 | Pfizer | Compuestos de benzolactama substituidos como antagonistas de la substancia p. |
| TW340842B (en) | 1995-08-24 | 1998-09-21 | Pfizer | Substituted benzylaminopiperidine compounds |
| AU722883B2 (en) | 1995-10-18 | 2000-08-10 | Merck & Co., Inc. | Cyclopentyl tachykinin receptor antagonists |
| DE19541283A1 (de) | 1995-11-06 | 1997-05-07 | Boehringer Ingelheim Kg | Neue Aminosäurederivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen |
| GB9523244D0 (en) | 1995-11-14 | 1996-01-17 | Merck Sharp & Dohme | Therapeutic agents |
| EP1019410A1 (en) | 1995-11-23 | 2000-07-19 | MERCK SHARP & DOHME LTD. | Spiro-piperidine derivatives and their use as tachykinin antagonists |
| GB9524157D0 (en) | 1995-11-25 | 1996-01-24 | Pfizer Ltd | Therapeutic agents |
| RU2135494C1 (ru) | 1995-12-01 | 1999-08-27 | Санкио Компани Лимитед | Гетероциклические соединения и композиция на их основе, проявляющая антагонистическое действие в отношении рецепторов тахикинина |
| GB9525296D0 (en) | 1995-12-11 | 1996-02-07 | Merck Sharp & Dohme | Therapeutic agents |
| ZA9610738B (en) | 1995-12-22 | 1997-06-24 | Warner Lambert Co | Subtype selective nmda receptor ligands and the use thereof |
| US6025355A (en) | 1997-05-19 | 2000-02-15 | Cambridge Neuroscience, Inc. | Pharmaceutically active compounds and methods of use |
| WO1997036876A1 (en) | 1996-04-03 | 1997-10-09 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| US5827875A (en) | 1996-05-10 | 1998-10-27 | Bristol-Myers Squibb Company | Inhibitors of microsomal triglyceride transfer protein and method |
| US5885983A (en) | 1996-05-10 | 1999-03-23 | Bristol-Myers Squibb Company | Inhibitors of microsomal triglyceride transfer protein and method |
| EP0906315A1 (en) | 1996-06-21 | 1999-04-07 | MERCK SHARP & DOHME LTD. | Spiro-piperidine derivatives and their use as therapeutic agents |
| DE19638484A1 (de) | 1996-09-20 | 1998-03-26 | Basf Ag | Hetaroylderivate |
| DE19638486A1 (de) | 1996-09-20 | 1998-03-26 | Basf Ag | Hetaroylderivate |
| WO1998035939A1 (en) | 1997-02-18 | 1998-08-20 | Sanwa Kagaku Kenkyusho Co., Ltd. | Malonic diamide derivatives and use thereof |
| US5907041A (en) | 1997-03-12 | 1999-05-25 | Rhone-Poulenc Inc. | Process for preparing pyrazole derivatives |
| JPH10292008A (ja) | 1997-04-21 | 1998-11-04 | Grand Polymer:Kk | α−オレフィンの重合方法 |
| CA2301548C (en) | 1997-10-07 | 2005-05-17 | Boehringer Ingelheim (Canada) Ltd. | Azetidinone derivatives for the treatment of hcmv infections |
| CA2301967C (en) | 1997-10-07 | 2005-05-17 | Boehringer Ingelheim (Canada) Ltd. | Azetidinone derivatives for the treatment of hcmv infections |
| US7041702B1 (en) | 1997-10-21 | 2006-05-09 | Scion Pharmaceuticals, Inc. | Pharmaceutically active compounds and methods of use |
| US6121261A (en) * | 1997-11-19 | 2000-09-19 | Merck & Co., Inc. | Method for treating attention deficit disorder |
| US6943159B1 (en) | 1998-02-18 | 2005-09-13 | Neurosearch A/S | Compounds and their use as positive AMPA receptor modulators |
| US6043253A (en) | 1998-03-03 | 2000-03-28 | Merck & Co., Inc. | Fused piperidine substituted arylsulfonamides as β3-agonists |
| WO2000014076A1 (en) | 1998-09-04 | 2000-03-16 | Ciba Specialty Chemicals Holding Inc. | Process for making 2,4-dihydroxyphenyl and 2-hydroxy-4-alkoxyphenyl substituted triazine compounds |
| JP2000186110A (ja) | 1998-12-21 | 2000-07-04 | Ube Ind Ltd | エチレン共重合体の製造方法 |
| WO2000041990A1 (de) | 1999-01-12 | 2000-07-20 | Clariant Finance (Bvi) Limited | Benzophenone und ihre verwendung als photoinitiatoren |
| US6664293B2 (en) | 1999-02-26 | 2003-12-16 | Fujiwawa Pharmaceutical Co., Ltd. | Amide compounds for the potentiation of cholinergic activity |
| US6586447B1 (en) | 1999-04-01 | 2003-07-01 | Pfizer Inc | 3,3-disubstituted-oxindole derivatives useful as anticancer agents |
| JP2001026580A (ja) | 1999-05-10 | 2001-01-30 | Sumitomo Chem Co Ltd | 光学活性1−アリール−1,2,3,4−テトラヒドロイソキノリン類の製造法 |
| US6562836B1 (en) | 1999-05-24 | 2003-05-13 | Queen's University Of Kingston | Methods and compounds for inhibiting amyloid deposits |
| AU5567000A (en) | 1999-06-24 | 2001-01-09 | Toray Industries, Inc. | Alpha1b-adrenergic receptor antagonists |
| EP1237547A2 (en) | 1999-07-09 | 2002-09-11 | Isis Innovation Limited | Compounds for inhibiting diseases and preparing cells for transplantation |
| US6340681B1 (en) | 1999-07-16 | 2002-01-22 | Pfizer Inc | 2-benzimidazolylamine compounds as ORL-1-receptor agonists |
| JP2001086110A (ja) | 1999-09-13 | 2001-03-30 | Toyo Commun Equip Co Ltd | 暗号化情報のパケット通信システム |
| MXPA02004330A (es) | 1999-11-03 | 2004-07-30 | Albany Molecular Res Inc | Tetrahidroisoquinolinas aril-y heteroaril-sustituidas y uso de las mismas para bloquear la recaptacion de norepinefrina, dopamina y serotonina.. |
| US7163949B1 (en) | 1999-11-03 | 2007-01-16 | Amr Technology, Inc. | 4-phenyl substituted tetrahydroisoquinolines and use thereof |
| NZ519146A (en) * | 1999-11-03 | 2004-02-27 | Albany Molecular Res Inc | 4-phenyl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine and serotonin |
| EP1248869A2 (en) | 2000-01-07 | 2002-10-16 | Transform Pharmaceuticals, Inc. | High-throughput formation, identification, and analysis of diverse solid-forms |
| AU2001262150A1 (en) | 2000-03-23 | 2001-10-03 | Mitsubishi Pharma Corporation | 2-(nitrogen-heterocyclic)pyrimidone derivatives |
| JP2003533513A (ja) | 2000-05-15 | 2003-11-11 | ダーウィン・ディスカバリー・リミテッド | Mmpおよびtnf阻害活性を有するヒドロキサム酸およびカルボン酸誘導体 |
| US6664256B1 (en) | 2000-07-10 | 2003-12-16 | Kowa Co., Ltd. | Phenylpyridazine compounds and medicines containing the same |
| KR100821410B1 (ko) | 2000-07-11 | 2008-04-10 | 에이엠알 테크놀로지, 인크. | 4-페닐 치환된 테트라하이드로이소퀴놀린 및 이의치료학적 용도 |
| WO2002046164A1 (en) | 2000-12-07 | 2002-06-13 | Astrazeneca Ab | Therapeutic compounds |
| US6506772B1 (en) | 2000-12-15 | 2003-01-14 | Hoffmann-La Roche Inc. | Substituted [1,2,4]triazolo[1,5a]pyridine derivatives with activity as adenosine receptor ligands |
| US6900220B2 (en) | 2001-01-02 | 2005-05-31 | Syntex (U.S.A.) Llc | Quinazolone derivatives as alpha 1A/B adrenergic receptor antagonists |
| US6911453B2 (en) * | 2001-12-05 | 2005-06-28 | Aventis Pharma Deutschland Gmbh | Substituted 4-phenyltetrahydroisoquinolinium, process for their preparation, their use as a medicament, and medicament containing them |
| US6974803B2 (en) | 2001-12-06 | 2005-12-13 | Pfizer Inc | Pharmaceutical combination |
| US6703405B2 (en) | 2001-12-22 | 2004-03-09 | Aventis Pharma Deutschland Gmbh | Substituted 4-phenyltetrahydroisoquinolinium salts, process for their preparation, their use as a medicament, and medicament containing them |
| US20050113283A1 (en) | 2002-01-18 | 2005-05-26 | David Solow-Cordero | Methods of treating conditions associated with an EDG-4 receptor |
| US20050261298A1 (en) | 2002-01-18 | 2005-11-24 | David Solow-Cordero | Methods of treating conditions associated with an Edg-7 receptor |
| EP1676844A1 (en) | 2004-12-28 | 2006-07-05 | Laboratorios Del Dr. Esteve, S.A. | 5-HT7 receptor antagonists |
| CA2478909A1 (en) | 2002-03-13 | 2003-09-25 | Duane D. Miller | Substituted tetrahydroisoquinoline compounds, methods of making, and their use |
| EP1852415B1 (en) | 2002-07-09 | 2009-10-07 | Lonza Ag | Process for the preparation of N-monosubstituted beta-amino alcohols |
| BR0313724A (pt) | 2002-08-13 | 2005-06-28 | Warner Lambert Co | Derivados de azaisoquinolina como inibidores de metaloproteinase de matriz |
| BR0313727A (pt) | 2002-08-13 | 2005-07-12 | Warner Lambert Co | Derivados de isoquinolina como inibidores de metaloproteinase da matriz |
| CA2499523C (en) | 2002-09-20 | 2011-04-19 | Medisyn Technologies, Inc. | Therapeutic agents and corresponding treatments |
| WO2004035812A2 (en) | 2002-10-16 | 2004-04-29 | Isis Innovation Limited | Asparaginyl hydroxylases and modulators thereof |
| GB0224557D0 (en) | 2002-10-22 | 2002-11-27 | Glaxo Group Ltd | Novel compounds |
| AU2003283646A1 (en) | 2002-12-02 | 2004-06-23 | Pharmacia & Upjohn Company Llc | The use of aryl- and heteroaryl-substituted tetrahydroisoquinolines in the treatment of chronic and neuropathic pain, migraine headaches, and urge, stress and mixed urinary incontinence |
| MXPA05005829A (es) | 2002-12-02 | 2005-08-29 | Pharmacia & Upjohn Co Llc | El uso de tetrahidroisoquinolinas 4-fenil-sustituidas en el tratamiento del dolor, dolores de cabeza migranosos e incontinencia urinaria. |
| DE10303254B3 (de) | 2003-01-28 | 2004-09-23 | Johannes-Gutenberg-Universität Mainz | 3,3-Dimethyl-8-oxoisochinoline, Verfahren zu ihrer Herstellung, sie enthaltende pharmazeutische Zusammensetzungen und deren Verwendung |
| CA2513684A1 (en) | 2003-01-31 | 2004-08-19 | Merck & Co., Inc. | 3-amino-4-phenylbutanoic acid derivatives as dipeptidyl peptidase inhibitors for the treatment or prevention of diabetes |
| US7241775B2 (en) | 2003-03-24 | 2007-07-10 | Sanofi-Aventis Deutschland Gmbh | Composition, process of making, and medical use of substituted 4-phenyltetrahydroisoquinolines |
| WO2004096774A1 (en) | 2003-05-01 | 2004-11-11 | Glaxo Group Limited | Acyl isoindoline derivatives and acyl isoquinoline derivatives as anti-viral agents |
| US7459460B2 (en) | 2003-05-28 | 2008-12-02 | Bristol-Myers Squibb Company | Trisubstituted heteroaromatic compounds as calcium sensing receptor modulators |
| JP2007530417A (ja) | 2003-07-01 | 2007-11-01 | プレジデント・アンド・フェロウズ・オブ・ハーバード・カレッジ | 細胞及び生物の寿命及びストレス応答を操作するための組成物 |
| US7501538B2 (en) | 2003-08-08 | 2009-03-10 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds, compositions and methods of use |
| US7973057B2 (en) | 2003-09-17 | 2011-07-05 | The United States Of America As Represented By The Department Of Health And Human Services | Thalidomide analogs |
| US7491794B2 (en) | 2003-10-14 | 2009-02-17 | Intermune, Inc. | Macrocyclic compounds as inhibitors of viral replication |
| JP2007008816A (ja) | 2003-10-15 | 2007-01-18 | Ube Ind Ltd | 新規イソキノリン誘導体 |
| ATE386715T1 (de) | 2003-11-25 | 2008-03-15 | Lilly Co Eli | Modulatoren des peroxisomproliferatoraktivierten rezeptors |
| US20050171027A1 (en) | 2003-12-29 | 2005-08-04 | President And Fellows Of Harvard College | Compositions for treating or preventing obesity and insulin resistance disorders |
| EP1723134A2 (en) | 2004-02-18 | 2006-11-22 | Pfizer Products Incorporated | Tetrahydroisoquinolinyl derivatives of quinazoline and isoquinoline |
| WO2005087235A1 (en) | 2004-03-09 | 2005-09-22 | National Health Research Institutes | Pyrrolidine compounds |
| AP2006003763A0 (en) | 2004-03-30 | 2006-10-31 | Intermune Inc | Macrocyclic compounds as inhibitors of viral replication |
| EP1750706B1 (en) | 2004-06-01 | 2016-10-05 | University Of Virginia Patent Foundation | Dual small molecule inhibitors of cancer and angiogenesis |
| US20060014705A1 (en) | 2004-06-30 | 2006-01-19 | Howitz Konrad T | Compositions and methods for selectively activating human sirtuins |
| NZ552397A (en) * | 2004-07-15 | 2011-04-29 | Amr Technology Inc | Aryl-and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| CN103251953A (zh) | 2004-07-19 | 2013-08-21 | 约翰·霍普金斯大学 | 供免疫抑制的flt3抑制剂 |
| US7211585B2 (en) | 2004-08-18 | 2007-05-01 | Laboratorios Del Dr. Esteve, S.A. | 5-HT7 receptor antagonists |
| US7211584B2 (en) | 2004-08-18 | 2007-05-01 | Laboratorios Del Dr. Esteve, S.A. | 5-HT7 receptor ligands |
| DE102004046492A1 (de) | 2004-09-23 | 2006-03-30 | Sanofi-Aventis Deutschland Gmbh | Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament |
| US20060111393A1 (en) | 2004-11-22 | 2006-05-25 | Molino Bruce F | 4-Phenyl substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine and serotonin |
| US20060111394A1 (en) | 2004-11-22 | 2006-05-25 | Molino Bruce F | Aryl-and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine and serotonin |
| US20060111385A1 (en) | 2004-11-22 | 2006-05-25 | Molino Bruce F | Novel 4-phenyl substituted tetrahydroisoquinolines and therapeutic use thereof |
| AU2005316337A1 (en) * | 2004-12-17 | 2006-06-22 | Janssen Pharmaceutica, N.V. | Tetrahydroisoquinoline compounds for treatment of CNS disorders |
| US20070060589A1 (en) | 2004-12-21 | 2007-03-15 | Purandare Ashok V | Inhibitors of protein arginine methyl transferases |
| JP2008528510A (ja) | 2005-01-20 | 2008-07-31 | サートリス ファーマシューティカルズ, インコーポレイテッド | 紅潮および/または薬物誘発性体重増加を処置するためのサーチュイン活性化化合物の使用 |
| AU2006215608A1 (en) | 2005-02-15 | 2006-08-24 | Novo Nordisk A/S | 3,4-dihydro-1H-isoquinoline-2-carboxylic acid 5-aminopyridin-2-yl esters |
| EP2805719A1 (en) | 2005-03-30 | 2014-11-26 | Glaxosmithkline LLC | Nicotinamide riboside and analogues thereof |
| DE102005025625A1 (de) | 2005-06-01 | 2006-12-07 | Friedrich-Schiller-Universität Jena | Neue hochaffine Dopaminantagonisten zur Behandlung der Schizophrenie und Verfahren zu ihrer Herstellung |
| KR101594898B1 (ko) | 2005-07-15 | 2016-02-18 | 알바니 몰레큘라 리써치, 인크. | 아릴- 및 헤테로아릴-치환된 테트라히드로벤자제핀, 및 노르에피네프린, 도파민 및 세로토닌의 재흡수를 차단하기 위한 용도 |
| US7425633B2 (en) | 2005-08-26 | 2008-09-16 | National Health Research Institutes | Pyrrolidine compounds |
| EP1924546A1 (en) | 2005-09-14 | 2008-05-28 | Amgen, Inc | Conformationally constrained 3- (4-hydroxy-phenyl) - substituted-propanoic acids useful for treating metabolic disorders |
| US20080255149A1 (en) | 2005-09-27 | 2008-10-16 | Novartis Ag | Carboxyamine Compounds and Methods of Use Thereof |
| WO2007048788A1 (en) | 2005-10-26 | 2007-05-03 | Laboratoires Serono S.A. | Sulfonamide derivatives and use thereof for the modulation of metalloproteinases |
| JP4955009B2 (ja) | 2005-11-11 | 2012-06-20 | エフ.ホフマン−ラ ロシュ アーゲー | 凝固因子Xaの阻害剤としての炭素環式縮合環アミン |
| WO2007098608A1 (en) | 2006-03-02 | 2007-09-07 | Chao-Jun Li | Chiral ligands, their preparation and uses thereof in assymetric reactions |
| EP2001866A2 (en) | 2006-03-29 | 2008-12-17 | Novartis AG | Organic compounds |
| JP5223083B2 (ja) | 2006-06-21 | 2013-06-26 | 国立大学法人京都大学 | 血管新生抑制剤 |
| US7919598B2 (en) | 2006-06-28 | 2011-04-05 | Bristol-Myers Squibb Company | Crystal structures of SGLT2 inhibitors and processes for preparing same |
| WO2008005368A2 (en) | 2006-06-30 | 2008-01-10 | Abbott Laboratories | Piperazines as p2x7 antagonists |
| ATE459352T1 (de) | 2006-07-04 | 2010-03-15 | Janssen Pharmaceutica Nv | Benzimidazol-cannabinoid-agonisten mit einer substituierten heterocyclischen gruppe |
| ES2576477T3 (es) | 2006-08-07 | 2016-07-07 | Janssen Pharmaceutica Nv | Proceso para la preparación de derivados de 1,2,3,4-tetrahidroisoquinolina sustituidos |
| SG174095A1 (en) | 2006-08-23 | 2011-09-29 | Valeant Pharmaceuticals Int | Derivatives of 4-(n-azacycloalkyl) anilides as potassium channel modulators |
| US8993593B2 (en) | 2006-08-23 | 2015-03-31 | Valeant Pharmaceuticals International | N-(4-(6-fluoro-3,4-dihydroisoquinolin-2(1H)-yl)-2,6-dimethylphenyl)-3,3-dimethylbutanamide as potassium channel modulators |
| DE102006046922B3 (de) | 2006-09-27 | 2007-11-15 | Julius-Maximilians-Universität Würzburg | Biofilm-hemmende Wirkung sowie anti-infektive Aktivität N,C-verknüpfter Arylisochinoline, deren pharmazeutischen Zusammensetzung und deren Verwendung |
| WO2008058126A2 (en) | 2006-11-06 | 2008-05-15 | Supergen, Inc. | Imidazo[1,2-b]pyridazine and pyrazolo[1,5-a]pyrimidine derivatives and their use as protein kinase inhibitors |
| CA2679735A1 (en) | 2007-03-01 | 2008-09-12 | Janssen Pharmaceutica N.V. | Tetrahydroisoquinoline compounds as modulators of the histamine h3 receptor |
| US7321064B1 (en) | 2007-03-08 | 2008-01-22 | Cedarburg Pharmaceuticals, Inc. | Preparation of amides of retinoic acid via mixed anhydride and mixed carbonate intermediates |
| NZ580802A (en) | 2007-05-10 | 2012-09-28 | Albany Molecular Res Inc | Aryloxy-and heteroaryloxy-substituted tetrahydrobenzazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| JP2010526825A (ja) | 2007-05-10 | 2010-08-05 | エーエムアール テクノロジー インコーポレイテッド | アリール置換およびヘテロアリール置換テトラヒドロベンゾ−1,4−ジアゼピンならびにノルエピネフリン、ドーパミンおよびセロトニンの再取り込みを遮断するためのその使用 |
| US7846930B2 (en) * | 2007-05-18 | 2010-12-07 | Janssen Pharmaceutica Nv | Diaryl-substituted tetrahydroisoquinolines as histamine H3 receptor and serotonin transporter modulators |
| EP2167083B1 (en) | 2007-06-06 | 2015-10-28 | Euthymics Bioscience, Inc. | 1- heteroaryl-3-azabicyclo[3.1.0]hexanes, methods for their preparation and their use as medicaments |
| US9156812B2 (en) | 2008-06-04 | 2015-10-13 | Bristol-Myers Squibb Company | Crystalline form of 6-[(4S)-2-methyl-4-(2-naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine |
| AR071997A1 (es) | 2008-06-04 | 2010-07-28 | Bristol Myers Squibb Co | Forma cristalina de 6-((4s)-2-metil-4-(2-naftil)-1,2,3,4-tetrahidroisoquinolin-7-il)piridazin-3-amina |
| WO2009155565A1 (en) | 2008-06-20 | 2009-12-23 | Genentech, Inc. | Triazolopyridine jak inhibitor compounds and methods |
| TWI453207B (zh) | 2008-09-08 | 2014-09-21 | Signal Pharm Llc | 胺基三唑并吡啶,其組合物及使用其之治療方法 |
| AU2010247763B2 (en) | 2009-05-12 | 2015-12-24 | Albany Molecular Research, Inc. | 7-([1,2,4,]triazolo[1,5,-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4- tetrahydroisoquinoline and use thereof |
| AU2010247735B2 (en) | 2009-05-12 | 2015-07-16 | Albany Molecular Research, Inc. | Crystalline forms of (S)-7-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)- 1,2,3,4-tetrahydroisoquinoline and use thereof |
| WO2010132437A1 (en) | 2009-05-12 | 2010-11-18 | Albany Molecular Research, Inc. | Aryl, heteroaryl, and heterocycle substituted tetrahydroisoquinolines and use thereof |
| US8691810B2 (en) | 2010-05-12 | 2014-04-08 | Abbvie Inc. | Pyrrolopyridine and pyrrolopyrimidine inhibitors of kinases |
| WO2012024397A2 (en) | 2010-08-17 | 2012-02-23 | Albany Molecular Research, Inc. | 2,5-methano-and 2,5-ethano-tetrahydrobenzazepine derivatives and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| WO2014159501A2 (en) | 2013-03-14 | 2014-10-02 | Bristol-Myers Squibb Company | Processes for preparing tetrahydroisoquinolines |
-
2005
- 2005-07-15 NZ NZ552397A patent/NZ552397A/en not_active IP Right Cessation
- 2005-07-15 MX MX2007000428A patent/MX2007000428A/es active IP Right Grant
- 2005-07-15 WO PCT/US2005/025193 patent/WO2006020049A2/en not_active Ceased
- 2005-07-15 EP EP05793999.3A patent/EP1778639B1/en not_active Expired - Lifetime
- 2005-07-15 UA UAA200701576A patent/UA91341C2/ru unknown
- 2005-07-15 CN CN201410074721.7A patent/CN103880827B/zh not_active Expired - Lifetime
- 2005-07-15 CN CN200580030990.2A patent/CN101119969B/zh not_active Expired - Lifetime
- 2005-07-15 GE GEAP20059847A patent/GEP20094640B/en unknown
- 2005-07-15 KR KR1020137001614A patent/KR101389246B1/ko not_active Expired - Lifetime
- 2005-07-15 BR BRPI0513359-9A patent/BRPI0513359A/pt not_active IP Right Cessation
- 2005-07-15 US US11/183,066 patent/US7541357B2/en active Active
- 2005-07-15 AU AU2005274927A patent/AU2005274927B2/en not_active Expired
- 2005-07-15 US US11/183,102 patent/US20060063766A1/en not_active Abandoned
- 2005-07-15 JP JP2007521686A patent/JP5007226B2/ja not_active Expired - Lifetime
- 2005-07-15 RU RU2007105596A patent/RU2388751C2/ru not_active IP Right Cessation
- 2005-07-15 CA CA2573271A patent/CA2573271C/en not_active Expired - Lifetime
- 2005-07-15 ZA ZA200701232A patent/ZA200701232B/xx unknown
- 2005-07-15 KR KR1020077003549A patent/KR101412339B1/ko not_active Expired - Fee Related
-
2006
- 2006-12-26 IL IL180349A patent/IL180349A/en not_active IP Right Cessation
-
2007
- 2007-02-15 NO NO20070877A patent/NO20070877L/no not_active Application Discontinuation
-
2008
- 2008-10-16 US US12/252,823 patent/US8227486B2/en active Active
-
2009
- 2009-04-02 US US12/417,598 patent/US8236796B2/en active Active
-
2012
- 2012-04-05 JP JP2012086151A patent/JP5552137B2/ja not_active Expired - Lifetime
- 2012-07-02 US US13/540,446 patent/US8741901B2/en not_active Expired - Lifetime
-
2014
- 2014-05-02 US US14/268,753 patent/US9085531B2/en not_active Expired - Lifetime
-
2015
- 2015-06-12 US US14/737,897 patent/US9499531B2/en not_active Expired - Lifetime
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2005274927B2 (en) | Aryl-and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin | |
| US9604960B2 (en) | Aryl, heteroaryl, and heterocycle substituted tetrahydroisoquinolines and use thereof | |
| AU781179B2 (en) | Aryl- and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine and serotonin | |
| HK1199253B (en) | Aryl- and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant or registration | ||
| GB | Transfer or rights |